This week I’m doing something a bit different. Not unhinged per se, but less “formal” than usual. I’m documenting 38 lessons across the areas of my life that matter the most to me.

Family. Craft. Habits. Community. Health. Values & Wealth.

Nothing here is earth shattering. It’s a mix of what I’ve learned that’s helping me live a full life. Take what’s helpful. Discard the rest like crumbs off the table, no offense taken. Maybe this is my own version of a “birthday card” to myself.

Happy 38th to me, and happy 38 lessons to you lucky readers.

Some of these are lessons I live by. Some I’m trying hard to put into practice (and fail). Some are aspirational.

Enjoy!

Up first is Family. The biggest “WHY” behind anything I do.

Family

1. The week stops on Friday night, complaining and all. Friday night dinner is the one thing in our week that stops, and everything gets prepped ahead (ahead meaning at least 10 minutes BEFORE said dinner time), so that when we sit down it’s mostly grape juice, bread, the blessings, talking and a whole lot of complaining. I grew up with Friday night dinner being a non-negotiable. We all had to be home for it, or join at a family friend’s. Not optional. No birthday party, movie night or hanging at a friend’s house was allowed to replace it.

What I remember from being a kid is that the week would be crazy, crazy, crazy, and then it would stop, and suddenly everything was quiet. I don’t have that quiet yet because my kids are little and LOUD, but I’m sure/hope it’ll come.

2. Be there for bedtime, and tell them stories about when we were little. Bedtime is one of those things so many parents struggle with, and yet when I’m not there for it, I miss it. Call me crazy, I know, but being there almost every night matters to me. My husband started this new tradition where he tells the kids his own crazy stories from when he was a kid. They love these and want them more than books. The only problem is that my said “retold” childhood stories are boring compared to his, so I’m often kicked out. All to say, I’ve made career choices, which is hard as a post-MBA mom, to be home for almost every bedtime.

3. Put the phone down, and make sure they notice. I try not to have my phone out when I’m with them, because if I’m telling them sitting on screens isn’t great, then I shouldn’t be doing it in their face, right? Also, I can only imagine what they see when they look up. Me just staring into the void, not present. I don’t want that to be the picture they remember. When my six-year-old says “hey, get off your phone,” it makes me happier than almost anything. He noticed. That’s THE point.

4. No screens during the week. Mostly. That’s the rule in our house. It’s the one people push back on the most and it’s the one I’d give up last. Except when they’re home sick, or we’re traveling, or on vacation, because I mean, how else does one feel better, travel or enjoy vacation? It’s all about balance.

5. Let them see you read. Stacks of books around the house, trips to the library together, and me reading on weekends. It may mean I max out the holds allowed by the Chicago Public Library (guilty) and have 10-15 checked out at a time (guilty again), but I know they’re watching me. So I read, real physical books, as often as possible.

6. Let them watch you build something hard. I want my kids to be proud of my work, and not because of what it pays, but because they saw me care about something, be bad at it, and keep going anyway. Which is exactly what these days feel like, though I’m a lot less bored than I was in tech and finance. Part of why I like writing this newsletter is that it’s documentation, and it’ll still be here when they’re old enough to read it. Hopefully they think I’m cool enough to read said documentation.

(Also, yes I did just write Not X But Y naturally - because that is what happens to one when they read too much AI written content).

7. Say sorry out loud. When I’ve done something that isn’t my best, I go back and own it. Not a vague “sorry if,” an actual “sorry I did X”. I’m big on internal locus of control and I try to teach them to take accountability instead of blaming others. So I try to model it myself.

When I've done something that isn't my best, I go back and own it. Not a vague "sorry if," an actual "sorry I did X."

8. Teach the cup half full, even about a wrongly peeled banana. When something goes wrong, which inevitably it does (and yes, sometimes it is a wrongly peeled banana, IYKYK), I try to give them the cup half full version. Not to talk them out of the feeling. Just to flip it and show them what the optimistic read is.

9. Celebrate on purpose. Make the trip, write the card, take the picture. I’m not a very emotional person, which is exactly why I have to be intentional about this. Getting to family for occasions is expensive. And exhausting. And still almost always worth it. And I’ve come around to kinda liking the printed photo albums, which 28-year-old me would have found hilarious. My kids love them even more.

10. Be at the school events. All of the MANY school events. Grandparents day, because we don’t have family in Chicago. The class parties. My parents always showed up even though they had busy work lives, and I remember that. So I show up to every one.

11. Marry someone who has the same value system. Plans change constantly and ours have changed plenty. Chicago nine years later was NOT in the plans, trust me. What’s mattered most is that my husband and I have the same values. Not necessarily the same goals. Values. This matters 10x more than you may think, especially once you start raising kids and see how values trickles in, FAST.

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Craft

I say craft on purpose, and not work. Craft is the work you enjoy, that gives you meaning, that you’re good at and want to get better at just because. It’s hard to find, and sometimes there’s a long road from work to craft. Work is where you show up every day, you’re decent (maybe great) at the job, the paycheck comes (sometimes it’s a BIG one), you go home, and you don’t think about it again until Monday. Unless the stress carries over. Craft vs work. Same hours. Completely different life and meaning.

12. The same activity can be work or craft depending on what it’s about. I used to have to write essays at school, in French, Hebrew and English. All about topics I didn’t care about, and I sucked at it. It stressed me out. Getting a B was a big deal compared to math and science where A+s were my jam. But now I write about things I actually believe and am living through, in my own voice. That makes it fun. My ability maybe changed slightly, but my why is a lot deeper. Which makes it craft and not work.

The same activity can be work or craft depending on what it’s about.

13. When someone laughs at my goals, I take the useful half. An older operating partner once laughed at me for wanting to build a certain business model. I said something like “I know that’s hard, but I may as well try,” and laughed it off. There was truth in what he was saying. People laugh off my big goals for two reasons. The first is that they see a real obstacle I haven’t seen yet, or am ignoring. The second is that they don’t know what I’m capable of. So now I go looking for the blockers I can’t see, and I ignore their read on what I can do.

14. Think 10x, even when it makes people uncomfortable. Borrowed from Benjamin Hardy’s 10x Is Easier Than 2x, which I highly recommend you read. Working out the next small step is useful for figuring out what has to happen. It just shouldn’t be the goal.

15. Grind in spurts. I did the grind in M&A advisory and I was SO exhausted. Tech I enjoyed a lot more because I was operating, though it was a little too slow-paced for me. I believe in a balance, meaning going very hard for a stretch is fine. Working long hours for the sake of working “late” is dumb.

16. Clear, measurable goals keep my time in check. Not willpower. I spent 5+ years operating in scorecards, KPIs, OKRs, EOS rocks (IYKYK), and what I miss about all of that is knowing whether the week was on or off track.

17. Working for yourself is really hard and I struggle with it every single day. I have rules about my mornings. Ideally no calls before 11am if I can swing it, nothing personal before 3pm (think appointments, the to-do list). From the outside it probably looks like a luxury, but it’s what keeps me disciplined. Some weeks I’m not good at holding it.

Habits

18. My whole system is one habit stack, and it runs at night. Skincare (thanks, Emily), then reading, then the journal, and in the journal three gains and three priorities and then what I’m grateful for, then a few quiet minutes of meditation (which is really me just listening to calming ocean sounds). The three gains come from The Gap and the Gain and they’re small on purpose. That small momentum helps me see progress on days when I’m TIRED. The three priorities are for tomorrow, and sometimes I hit them and sometimes I don’t. But I get in bed knowing roughly what tomorrow is “supposed” to be, and I’ve wound down.

19. Saying yes to everything is like doing a lot of nothing. I’m not on school boards. I’m not volunteering for everything. When I say yes now it’s because I believe in it and think I can add real value. Saying no is the newest skill I’ve had to build. There will be time for those activities, but this is just not the season for it.

Saying yes to everything is like doing a lot of nothing.

20. Hours don’t equal productivity. Not a new idea, I know. I’m listing it because I spent YEARS living like the opposite was true, and what finally worked was to stop counting hours and start noticing whether I was in flow or just present. Flow for the win. Hours for the loss.

21. Walk for ten minutes with nothing in your ears. Ten or fifteen if I’m lucky, ideally before I sit down to work, and no phone, no headphones, no podcast. That way it can be quiet (minus the street noise).

22. My office used to be a closet. A really messy one. This weekend my husband redid it and now it’s a proper working space. I hate clutter. I’m always pushing things out of the house. Having less really is having more, and it turns out that’s true about a lot more than closets.

Community

23. Sending a meal when someone is going through something matters. A LOT. After my first was born it was hard, and we’d just moved, and my community put together a meal train and food arrived at the door for WEEKS. I barely knew some of them. I do it for other people now when I can.

24. Being part of something bigger gives me something to fall back on. I never know which week I’m going to need the extra support, especially living in a city with no family. Which is exactly why I try to show up and build it when I don’t need it.

25. Different people plug into different pockets of my life. Some friendships are professional, some are personal, some are extensions of the kids and school life. Friendships don’t need to be all the things all the time, and realizing different ones serve different purposes has been freeing.

Friendships don't need to be all the things all the time.

26. My kids are learning to talk to adults and have no idea it’s happening. The Friday nights I remember most from growing up were the ones with other people there, because that’s where I learned to hold a conversation with someone much older than me and someone much younger than me in the same hour. My kids are getting that now, which is the best.

Nothing like some fresh air and a view to reset.

Health

27. Health is a lot more than my macros and how much I can lift. It’s my mental health, my spiritual health, my anxiety level, my sleep. I spent a long time measuring the two things that were easiest to measure.

Health is a lot more than my macros and how much I can lift. It’s my mental health, my spiritual health, my anxiety level, my sleep.

28. I can’t keep doing the same things. I don’t train the way I used to, mostly because things just hurt more now. Being stubborn about my old plan didn’t serve me well, so I’ve adjusted to what my body needs now. Also, a healing broken toe doesn’t help.

29. The same bedtime routine beats the number of hours, with a caveat. My ideal is nine, I’m getting seven to eight, but I get in bed at about the same time every night. Doing said boring routine above. Consistency of when I get into bed matters more than how much I sleep. Mostly.

30. Loosen the food rules. I used to be a lot more restricted about it (IYKYK) and now I watch macros at a high level and stop there. I’m both healthier AND significantly less annoying to have dinner with. Pass the pasta, please?

31. Almost entirely off social media. Except LinkedIn. I cut TV and I’m still working on the scrolling (LinkedIn is my one guilty pleasure). These two have done more for my attention than any productivity system I’ve ever tried.

Values and wealth

32. Having less is really having more. We carry so much stress from wanting more, and more, and more. So many of our problems could be solved by wanting less.

So many of our problems could be solved by wanting less.

33. There’s more than one kind of wealth and mine won’t look like yours. Time, money, health, family. I’ve been reading Sahil Bloom on this and I highly recommend it. What I’d add is that so much of it is circumstantial, so the real work is figuring out what’s good enough for YOU instead of measuring against what everyone else has.

34. Before anything big: do I want it, or do I think I’m supposed to have it? And how does it actually improve my quality of life? If it’s big I ask more than once, on different days. Ask my husband though, he may disagree and say I’m not actually Zen enough sometimes.

35. Save for the rainy day. Sounds vanilla. It is. Nothing better than having funds set aside, and still spending on the things that matter.

36. I pay more for less space, on purpose. We live in the city, which costs more and gets us less room. Suburbs folks, I know you all think we’re nuts. We do it because it gets us the most time with our kids before and after work. That’s our version of utility. Someone else’s is a big yard and a longer commute and that’s a completely fine answer, it’s just not ours. For now.

37. Spend on the things that keep paying me back. I spend money on being able to be with my kids, on being healthy, on doing work I care about. I spend a lot less on stuff, which feels great in the store and then, pretty reliably, doesn’t once it’s home.

38. Playing a game that isn’t mine is the dangerous one. I have to be very cognizant of not getting my priorities quietly mixed up with someone else’s. I see what others are building, how fast it “looks” like they’re moving. And sometimes I get jealous. But I try to remember that I’m playing my game, not theirs. Comparing shows up in so many places. Careers, money, health, fitness. The only fix I’ve found is asking myself whose game this is. I ask it more than I like to admit.

Playing a game that isn’t mine is the dangerous one.

That’s 38. Some of these are fresh, some I’ve known for years. And a good few are ones I wrote down hoping I can internalize them fully one day.

If five of them resonate with you, take those five and forget the other 33. That’s how I read other people’s lists too. But for some reason, to this day, I love a good list.

Save this one. And if you’ve got a birthday coming up, try writing your own version, it’s a much better exercise than I expected it to be.

I’ll see you after carpool.

Danielle

Your company gave you Claude. Then you caught yourself talking like it.

Guide 4: the file that keeps your writing sounding like you, and the loop that keeps it honest.

I write my Notes on Substack the old-fashioned way. I sit down with my pillars in front of me, I don’t open anything else, and I just write. It’s a good exercise and I like doing it.

Which is why it freaked me out a little when I started finding AI-isms in my own writing. “It’s not X, it’s Y,” sitting right at the front of a sentence, unprompted, from ME. Then I caught myself saying it out loud in a real conversation. I’ve been reading so much AI this year that I’ve started to sound like it, and I’m the one who’s supposed to be catching this stuff. (I wish I was making this up.)

Here’s the part I’d rather skip. I’m not the best writer. When I started the newsletter I leaned on AI to get me going, and a big reason I can write more naturally now is all that back and forth - draft it, rework it, look at what I changed. So I’m semi-okay with how I got here (and I’d do it the same way again). What I’m not okay with is sending something out that doesn’t sound like how I’d really write and talk.

I can also tell when someone else hasn’t done it well. I’ll be reading along and get to a story that’s technically right but not personal enough, where the perspective is so general it could be anybody’s, and I get the ick and I skip it. IYKYK. That reader is me, and that reader is also everyone on your list and everyone who opens your business review. And if you’ve started catching it in your own writing, same.

(New here? Guide 1 builds your second brain, and its My Voice page is the file this guide sits on. Start there.)

Nobody is putting spell check back in the box

Everywhere you look right now, someone is telling you to stop writing with AI. I think that’s wrong, and I’d be a hypocrite anyway, because I use it every single day.

Telling people not to write with AI is like telling them to turn off spell check. Of course you’re going to run spell check before you put something out.

And the output is GOOD, which is exactly what makes this tricky. It tightens up the sentence you would have shipped anyway, and it flows better than your third paragraph was going to. What it can’t do is have your judgment, so what comes back is the average of everybody, and the average of everybody is what I scroll right past.

Alex at Tenex changed how I think about this. He built an amazing newsletter and now he runs an AI agency putting this stuff into some of the largest companies in the world, and he walks through exactly how he balances his own voice against the things he cares about when he writes. Watching someone that good at this use AI on purpose was the thing that did it for me. All we see online is AI slop, AI this, AI that, and I get nauseated by it too, but it’s a tool, and the question is how you use it and how much intention you bring. The voice-file idea itself I took from Ruben Hassid (I am just a text file, and it’s not X, it’s Y is the best list of the giveaways I’ve seen - I highly recommend both). I didn’t invent any of this. I just run it.

The only test I trust: would I say this out loud?

Here’s a real example I’m going to share. My last edition, the camp/color war edition. The draft came back with a header that said “The Scarce Thing Isn’t Knowing Anymore.” Like, I would never say that. Not to you, not to a friend standing outside at school pickup.

What I would say, and what the edition ended up being called, is “Everyone’s prepping their kids for AI. I’m sending mine to camp.” That’s how I talk. It also happens to be what the piece was about, and that’s the other thing that goes wrong when a line isn’t yours: the wrong header had moved the entire edition onto a topic I wasn’t even writing about.

Same pass, I cut “future-proof,” “the ground is moving,” “it clicked,” “kept showing up,” and “underneath the doing.” None of them are bad writing. They just sounded finished before they had a thought in them, and every one of them failed the same test - I read it, I heard myself saying it, and it died in the air.

Ruben’s list of the universal tells is worth knowing (the “it’s not X, it’s Y” flip, the tidy group of three, the em dash doing rhythm work nobody asked for, the puffed-up words). But the one that’s the most meaningful for me is the one that’s based off the sentences I have literally cut out of my own editing before, because if I don’t do that, it’s possible they’ll pop right back up. And I don’t want that to happen.

Three steps, and the third one is why I wrote this

Step 1: Upgrade the file you already built

Guide 1 had you make a My Voice page. It’s version one and it’s supposed to be thin, so what we’re going to do here is go back, tighten it, and make it even more meaningful.

Open my My Voice file. Interview me to make it sharper, in small batches, and I’ll answer out loud. Cover the words and phrases I use constantly, the ones I’d never say, my hard NOs, and what I refuse to sound like. Keep it specific and quotable, not a description of a nice person. Where I’m vague, ask me again.

Answer by talking, not typing. The way you talk IS the raw material, and typing cleans it up before it ever gets to the page.

Step 2: Feed it the writing that isn’t smooth

Most people upload their three most polished pieces and then wonder why what comes back doesn’t sound like them. No surprise. Polished writing is where you sound the most like everybody else.

When I looked at my own writing, it was crazy run-on sentences. Some of them are super choppy. I had caps in there from when I was VERY excited. The flow was weird in some paragraphs and honestly horrible in others. And that talks like me. I talk very fast, and it turns out I write fast the same way. All of that is the part that sounds like me, and it’s the first thing a model tidies away if you don’t tell it not to.

So give it the diversity - the range of how you talk and how you write - sorted by what it was for. I use AI hardest on the two places where it matters most for me: getting something complicated across in a business review, and writing the copy for my own website so it still sounds like a person wrote it. Yours might be the update to your manager, the exec summary, the doc where you’re making a hard case. Give it the good version and the tired version of each.

Here’s a batch of my real writing, sorted by what it was for. Read it against my voice file and add what you find: sentence length and rhythm, punctuation habits, how I open and close, my go-to words, where I get uneven, and anything I never do. Show me the additions before you write them in.

If you talk more than you write, feed it voice notes. A transcript of you thinking out loud is the least edited sample of yourself you own.

(Optional, and worth ten minutes: a second file for who’s on the other end. I keep one for my newsletter reader, because writing that sounds like me but lands nowhere is still a miss.)

Step 3: The diff loop

Every time I let AI draft something, I keep the draft. Then I rework it, again and again and again. And my version comes out different in ways I couldn’t have described to you in advance, so I hand both back and ask what changed.

I’m giving you two versions of the same piece: your draft, and my final after I reworked it. Compare them line by line and tell me what I consistently changed - word choices, sentence length, what I cut, what I added, what I softened. Write the patterns as rules in my voice file, and if you see the same pattern twice, mark it confirmed.

The answers become my own rules, the rules go back in the file, and the next draft starts from a version that took into account all of my ways of not talking. That’s what makes sure that every single time I sit down to write something meaningful in long form, it’s really writing how I would naturally write.

Mine is a real file with a date at the top and a log at the bottom (it’s called AAC Voice Edit Tracker, which is not a super cool name, but it works). It’s how I know things about my own writing that nobody ever told me: that I break a long sentence with a spaced hyphen and never an em dash, that I add a caveat in parentheses so I don’t get misread, that after I admit something hard I always turn it forward. I didn’t know any of that about myself until the diff showed me, twice.

What this is protecting

Use the tool, run the spell check, let it tighten your sentences.

But what you’re building underneath all of it is the version of you that’s portable - your judgment, your taste, the way you land a point. That’s what walks out the door with you when the title changes or the org chart moves, and it’s the one thing on your laptop that can’t be regenerated. Protecting it is the same as protecting whether people trust you, because a reader who clocks you as generic doesn’t argue with you. They just skip you, the same way I do.

So go find your My Voice file from Guide 1 and give it fifteen honest minutes out loud (fifteen, that’s it). Then the next time you let AI draft something real, keep both versions and ask it what you changed. That second habit is the one that compounds, and it costs you about two minutes a draft.

Save this. Send it to the person on your team whose messages have started to sound like everybody else’s.

If I made the full version of this, templates and the full system, would you want it? Hit reply and tell me which part.

I’ll see you after carpool.

- Danielle

(Waterfront image of the sleep away camp I went to for years)

Color war was the best part of my summer, every single summer. The relay races, the gaga ball and nukem ball tournaments, the camp-wide race where they’d get every last kid out on the field at the same time and the energy was magical. I loved the competition, I loved being on a team, and I really loved the cheering. I was a shy kid in a lot of ways, but color war was the one place that shyness dissipated. I got so into it over the years that I ended up as one of the color war captains later, in high school (yes our school had color war - weird, I know).

Decades later (I’m aging myself here), the feeling of color war is what comes back first, being part of something bigger than me and coming back to enjoy the camp feeling year after year. And it’s what I find myself wanting to give my own kids right now, in a summer where the news and noise around AI tells us the world is changing FAST. I keep reading that if I really cared about the future my kids are walking into, I’d be getting them ready for AI. Coding camp, an AI tutor, the earlier the better. I use these tools all day for work, so believe me, I feel that pressure as much as anyone. But when I look at what I’m giving my kids this summer, it’s camp. Plain, sweaty, sunscreen-in-your-eyes summer camp.

My six-year-old is wrapping up week 7 of 7 of his camp experience. He’s obsessed with the theme days and the camp-wide color war and the gaga ball games, same as I was. The one thing he didn’t love, at least at the start, was swimming (I always hated waterfront - you could find me on the sports field instead). He was in the water five days a week and he made sure I knew how he felt about it most of those days. I didn’t let us make a big deal out of it. The pressure stayed low (but he still had to show up), and he slowly came around. Now he loves swim time. It just took him doing it over and over, badly, before he got there.

The Feeling a Screen Can’t Give Them

Here’s what I keep finding when I think about summer. Almost everything I remember from camp, and everything I’m watching my son pick up right now, is the stuff no screen can give you. Getting along with kids you didn’t choose in your group or bunk. Trying something you’d never sign up for on your own (swim 5x a week being one), in a place safe enough to be bad at it for a while. Feeling like you’re part of something bigger than yourself. We even had a word for that feeling, Ruach, which is Hebrew for spirit, and there’s no version of it that an AI bot or downloadable app can give a kid.

That’s the exact thing I worry AI steals from our kids. When I don’t feel like sitting or wrestling with something hard, I can open Claude and have an answer in a few seconds, and most of the time, I take it. Our kids are growing up with that option built in from day one. That’s not great.

Camp builds the muscle of showing up again when the answer isn’t instant or when the experience is uncomfortable. AI is the thing that lets us stop building those skills.

What I really want to know, underneath all the noise in the news and on my feeds, is whether I’m giving my kids the experiences and skills that matter most to ME. A sense of community. Being a good person who does good things for people, not just talks about it. A love of learning, and even more than that, a love of asking questions. I grew up in a house full of questioning, and I would hate to give that up and have a generation of kids who got great at getting answers and never had to work at a hard one long enough to figure it out on their own.

I can’t tell you which jobs will be around when my kids are grown, or what any of these tools will look like by then. Heck, I’m not sure we have any clue what that will look like five years from now. What I do know is that they’ll need to get along with people they didn’t pick, stick with something hard, and figure things out when nobody’s just giving them the answer right away. Camp has always built exactly those skills, and as long as we keep it tech free, it always will. That ability to slow down and stay analog while the technology keeps moving at warp speed ahead is priceless.

What Happens When You Take the AI Away

Last year a group of researchers in Turkey (Bastani and his co-authors) gave about a thousand high schoolers GPT-4 to practice math with. While they had it, they did great, close to 48% better than the kids without it. Then the researchers took it away for the real test, and those same kids scored worse than the ones who never used it at all, by around 17% (zero shocker given how I feel after using AI too much). That kind of false confidence, riding high while the AI is there and crashing the second it’s gone, is exactly what scares me.

The one exception was a version that only gave hints instead of full answers, and those kids kept their gains. They put out a correction later, so I don’t want to lean too hard on the exact numbers, but the basic shape of the study matters. The help that feels best in the moment can be the help that leaves you with the least. Which I think resonates with how a lot of us feel with the constant tug of “how much do we help our kids before it’s too much.” It’s finding that balance of building resilience but being supportive.

The help that feels best in the moment can be the help that leaves you with the least.

None of this makes AI the villain, by the way. The hint-only version worked fine, which makes sense. A tool with a little friction built into it can really help, and I see that for myself when using it for work. A tool that does every single step for you takes something with it along the way.

Camp has its own proof, for what it’s worth. In one study, Uhls and her colleagues sent a group of kids to a screen-free camp for five days, and afterward they were noticeably better at reading emotions on other people’s faces than a matched group who stayed home with their devices. Five days. That was all it took. Which tracks, because I always said the best place to learn EQ is at sleepaway camp.

(Our summer tradition of spending weekends at the beach when schedule allows, hands down the best part of Chicago living).

About That AI School I Was So Into

A while back I wrote to you about the new AI schools, the kind where software runs the day and there’s no teacher at the front of the room. I was into it. I’m walking that back a little now, if I’m honest. The more I use these tools for real work, the more I see how fast this is all moving and how much we still don’t really know.

And when you look closely at the most talked-about of these schools, a few things stand out. The “AI” doing the teaching is mostly adaptive practice software, closer to Khan Academy than to ChatGPT. Tuition runs anywhere from forty to seventy-five thousand dollars a year depending on the city (Chicago is sitting at $55K a year, where I live). And the super impressive results they advertise (which, I’ll be honest, got me excited in the first place) haven’t been checked by anyone on the outside. I’m all for fact checking, and there isn’t really a control group here, so I’m back in wary-but-watching mode. Victor Lee, who studies this at Stanford, calls it an effective model with real limitations, and makes the point that a private school at that price is largely teaching kids who were already going to test well (that opens a whole other can of worms I’m not going to dig into today).

A real school still matters, and I’m guessing that’s because resilience, EQ, and emotional discomfort get “experienced” in that environment. The schools of the future don’t have to be AI schools per se. But what IS top of mind for me, what I care about, is how we get the good technology into the schools we already have, so every kid gets it (mine included). And not leave it just for the kids whose families can pay these wild prices.

The Four Things I Lean On All Summer

So no, I’m not running some off-grid, no-technology summer over here. And I’m not going the other extreme and plopping my kid into some crazy expensive AI-driven school.

I do know my kids will use AI in ways we can’t imagine right now. But here are the ways I’m taking the lessons from summer and building them into our school year, so they’re prepared for the future of work and life, whichever way it plays out:

1. The director. I let AI run the planning and the logistics (with tight control on safety) so we can live life more fully. That’s the routine follow-ups, scheduling, activity planning, and lunch ordering (hopefully more than just a cookie - IYKYK). But mostly, having it find the really fun activities that aren’t on my radar and fit into our days (think my summer bucket list artifact).

2. Friday night dinners. This is the one thing none of the technology touches. It’s what I grew up with, the whole family around the table, same night every week. It was always tech free by default. It’s something I’m trying to keep even when I’m too tired to plan and cook, because this tradition really rooted me in who I am and gave me quiet, intentional time with my parents, siblings, and our family friends.

3. Removing things. Before I sign us up for one more enriching activity, I try to take something off the calendar first. So much of the good stuff at camp happens in the boring, unstructured in-between, and it’s the same at home. I add a lot less than I used to, and I’m very conscious of not over-planning.

4. One waterfront a “season.” There’s always one tradition I hold onto even when the kids say they don’t want to. This season it was the water, weekly swim lessons (on top of camp swim) and the ritual of going to the beach (it’s a 6-minute drive from us, probably the only great thing about Chicago). They were not into swim back in June. I kept it on the calendar anyway, and now it’s turned into something they look forward to each week. My goal is to find this equivalent in every season.

Where I’d Start

If you take one thing from all of this (which, I’ll admit, feels more like a nostalgic post, because that’s the mood I’m in), I’d make it the Friday night dinner, or honestly any night of the week that works. It’s the easiest one to start and the hardest one to regret. Put it on the calendar, phones by the door, and then, once everyone’s there, ask the kids what they love about camp, or about color war, and how you might carry some of that summer feeling with you through the rest of the year. Then just listen. You’ll learn more about who they’re becoming through that quiet weekly dinner ritual. Feels kind of 70’s/80’s era, but it’s awesome.

What I want for my kids, more than any head start, is for them to have a color war of their own. Some team, some week, some thing they cheer their hearts out over and keep coming back to year after year, long after they’ve forgotten whatever was on a screen that summer.

I can want real guardrails around what these AI tools do to my kids and still want them ready for a deeply technical world. There’s a place for both. The way I get them there is by protecting the low-tech, hands-on stuff that builds the steadiness to handle whatever comes. So I’m sending mine to camp. I’m not worried they’ll fall behind for spending July on a field instead of in front of a screen learning to code. If anything, they’re getting the skills that will carry them into whatever this world becomes.

And the fact that you’re even asking whether you’re doing right by them, in a summer when everyone is telling you to prep them for a future none of us can really picture, tells me you’re paying attention.

I’ll see you after carpool.

Danielle

Your week is already your newsletter. Here’s how to publish it.

Guide 3: the weekly AI system that turns your real life into an edition that sounds like you.

I run an AI and fractional COO agency, and on the side I’m looking at some business investments. This newsletter is just my pastime, the fun thing I do that has nothing to do with either.

Which is kind of funny, because writing was never my thing. I was a math and science kid who dreaded every paper in school, and I still think way faster in numbers than in words.

So when I started AI After Carpool, the writing itself wasn’t the scary part. The scary part was doing it again the next week, and the week after that, when I’m already running a company, looking at deals, raising three kids, and it’s 9pm with nothing left. That’s where most newsletters die, on the week you’re just too fried to write one.

Most people just open a blank chat and ask AI to write the newsletter for them. I get why, but you can always tell. It comes back smooth and fine and sounds like nobody, and nobody forwards that.

So I do it almost backwards. I don’t start with AI, and I don’t end with it either. AI sits in the middle. First I pump in a ton of my own stuff, the real moments from my week, my actual take, the way I’d say it out loud. Then AI takes all of that and writes the first draft. And then the real work starts, where I go back through the whole thing and rewrite it the way I actually would, like an editor with a red pen. The start is me, the middle is AI, and the end is me again.

This is all of it, the real steps, the actual prompts, and one new piece I’m still testing that I stole from someone in the content world. If you’ve been meaning to start a newsletter, or you’ve got one and every week feels like starting over, this is how I’d do it.

(New here? This works on its own, but it runs on the second brain from Guide 1. If Claude already knows your voice and your reader, all of this gets sharper.)

First, the one idea it all runs on

You feed it, and you finish it. AI just drafts the middle.

The stuff that used to stop me from hitting publish, figuring out what to write, staring at a blank page, the endless title tweaking, AI can carry all of that. But the two things that actually make it mine, everything real I put in at the start and the full rewrite at the end, never leave my hands. AI gets the messy middle, and it never gets the first word or the last word.

Every step below protects that. This isn’t about handing your newsletter to a robot. It’s about owning the start and the finish, and letting AI take the slog in between, so you never face a blank page and you’ve still got energy left for the part that makes it yours.

Wait, what’s a “skill”?

I’m going to say the word skill a lot, so here’s the quick version. A skill is a saved job you run with a slash command: you type /, pick it, and Claude does that one task the same way every time, no re-explaining. You set it up once and you’re done.

You don’t code it, you just talk. Tell Claude what you want it to do (run /skill-creator), or when it nails something, say “save this as a skill.” That’s it.

This matters for a newsletter because it’s the same few jobs every week: find the topic, pick the title, sharpen the take, draft it, edit it, publish it. Turn each one into a skill, and your week stops being “write a newsletter from scratch” and starts being “run down the list.” The system gets it out the door, not whether you feel like it on a Tuesday.

The whole setup, on one page

It’s a chain of small skills that hand off to each other, six skills and one habit, and most weeks I’m not even thinking about it, I just run it.

Every step is only as good as what the one before it handed over. Let me walk you through mine.

Step 1: Document the week (a habit, not a skill)

Honestly, everyone skips this step, and it’s exactly why their AI drafts come out flat. I skipped it too at first.

Now I leave myself a trail all week. Not a journal (I’d never keep a journal), just little breadcrumbs I drop the second something happens: a line one of my kids says in the car, a screenshot of something I saw waiting at pickup, two sentences I thumb into my notes app because a work thing suddenly clicked with a parenting thing, a photo of a page in whatever I’m reading.

A draft comes out generic when you didn’t give it anything real to work with, so it grabs the most average version of your topic and runs with it. Specific beats smart every time, and while AI can polish all day, it can’t make up the thing that actually happened to you on Tuesday, because it wasn’t there. You were.

So catch it in the moment, and talk it out instead of typing it, because you talk way faster than you type and the messy stuff you’d never bother writing down is half of what makes it sound like you. Dump it all in one note, wherever you already live, and by the weekend you’re not staring at a blank page, you’ve got a pile of real stuff to pull from.

Step 2: The Trend Scanner (what to write about)

I read a lot, Justin Welsh, Sahil Bloom, James Clear, a bunch of AI newsletters, plus whatever’s blowing up that week. But a pile of stuff I read isn’t a topic, and what I needed was a way to cut through all of it and land on the one thing actually worth writing about, for my reader.

A trend scanner is a skill that works like a little research assistant you send out every week, and it does two things at once. It plays private investigator on the internet, hunting down the news and conversations that are actually trending in your corner of the world. At the same time, it reads back through my own notes from Step 1 and finds the patterns I didn’t realize I kept circling. Then it weaves the two together, what’s moving out there and what’s already on my mind, because spotting patterns and connecting dots is the one thing AI is genuinely great at.

The other half of it is the reader. Mine’s built around one person, Megan, and I’ve got her written down in detail, what she wants and what she’d roll her eyes at. Every trend has to get past her: would she stop for this, could she use it by Friday, does it make her feel more capable instead of more anxious? If it can’t pass Megan it’s out, and that’s what turns “here’s what’s trending” into “here’s what you should write.”

Build a skill called trend-scanner. When I run it, search the web for what’s
happening this week in [your topic], but filter everything through my specific
reader: [a short description of who they are, what they want, what they’d
never care about].

Hand me a short brief, two pages max:
- The top 4 or 5 things worth writing about this week, plain language,
  opportunity-first, never fear-first.
- For each, the specific angle for my reader and the one concrete thing they
  could actually do with it.
- Any expert or named source that makes it credible.
- End with 2 or 3 mapped into a rough direction, plus a few possible titles.

Also read my running notes from this week [point it at your capture doc] and
weave in anything I captured. My real moments beat anything online, lead with
those where they fit.

Then I read the brief and pick a direction, not the final title yet, just what this week’s about.

Step 3: Lock the hook before you write a word

I did this backwards for months. I’d write the whole newsletter and then try to come up with a title at the end, which is a bad idea, because by then the thing’s wandered all over and you’re just slapping a title on whatever came out.

So now the title comes first, and it’s its own skill. I lock the title and subheader before I write a word, and everything after that gets built to pay it off.

The skill spits out about 20 titles across different angles (not 20 versions of the same one), scores them, and gives me the best 5, each with a subheader. The subheader matters more than you’d think, because the title makes you curious and the subheader tells you what you actually get. And one thing I learned the hard way: the title that sounds best isn’t always the one you have the most to say about. So I hold the 5 and lock the real one in the next step, after I’ve heard myself talk.

Build a skill called hook-titles. From this week’s trend brief, generate 20
title options across different angles, not 20 versions of one idea. All in my
voice, nothing that sounds like a guru or a LinkedIn hustler.

Score them and give me the top 5, each with one or two subheaders. The title
opens the curiosity, the subheader makes the promise concrete. Recommend one,
tell me why in two lines. Invent no detail, story, or number that isn’t real,
flag it instead. Hold the 5 as candidates. I’ll lock one after the interview.

Step 4: The Carpool Council (the new step)

This is the piece I’m most excited about, and it’s new, so fair warning, I’m still testing it. I stole the idea from the content world and made it my own.

It’s simple. Before I write, I sit for an interview, not with a person, but with a little panel of voices I put together on purpose, and their whole job is to drag my real take out of me. I call it the Carpool Council, four seats, and it runs right after I’ve got my title options.

When a draft comes out boring, it’s almost never the writing, it’s that nobody pulled your real take out of you first. This gets mine on the table in ten minutes up front, instead of a two-hour rewrite at the end. The one rule is that the panel never writes, it only asks, and if a seat starts writing sentences for me, I stop it and send it back to questions.

Two seats pull the take out of me, two guard the reader. The systems seat pushes for the exact steps someone could copy, which tool, what I did first, what the prompt actually said. The courage seat asks what it cost me or scared me before I did it, which is where the honest part comes from.

Then the guards come in, after I’ve talked. The reality guard asks whether this is even true today, and still true in three months. The evidence guard asks for the proof, and what a skeptic would say.

The best part is in the middle. After the first two seats dig in, the Council tells me which two or three titles I clearly have the most to say about, and I lock one. That’s when the title actually gets decided, because now I’ve heard myself talk.

And it doesn’t hand me a draft, it hands me a brief, and it’s the most useful page of my week:

LOCKED HOOK:      [your final title and subheader]
THE THESIS:       [your take, your words, a sentence or two]
THE PROOF:        [the specific story, example, or number behind it]
THE MECHANICS:    [the replicable how, from the systems seat]
THE EMOTIONAL     [the cost, the stakes, the real moment, from the
CORE:              courage seat]
THE HONEST        [the limit, the caveat, the counter-argument you’re
CAVEAT:            not dodging, from the guards]
THE READER        [what your reader walks away able to do]
PAYOFF:
RAW QUOTES:       [3 to 6 of your own lines, word for word]

That RAW QUOTES section is a week of social posts sitting right there. Don’t mine your finished newsletter for social later, it’s already been smoothed out, so mine the interview instead, because what you said out loud already sounds like you.

Build a skill called carpool-council. Runs after I have my hook candidates and
my notes for the week. Your job is to interview me, not to write. Never draft a
sentence for me. If you catch yourself writing prose, stop and go back to asking.

Four interviewers, one at a time. Two extract, two guard.
- Extract, the system: push for the exact steps, the specific tool, the real
  sequence someone could copy.
- Extract, the courage: push for what it cost me, the honest moment, the stakes.
- Guard, reality: pressure-test whether it’s true today and in a few months.
- Guard, evidence: pressure-test the proof, and what a skeptic would say.

Run the two extract seats first, each one opening question and up to three
follow-ups, digging till satisfied. I answer out loud. Then, mid-session, name
the 2 or 3 hooks I clearly have the sharpest take on and have me lock one. Then
run the two guards against the locked take. Cap it near ten minutes of me talking.

Output only the brief: locked hook, thesis, proof, mechanics, emotional core,
honest caveat, reader payoff, and 3 to 6 of my own verbatim quotes.

Answer these out loud, by voice, so your real way of talking ends up in the transcript, because that’s what keeps the draft sounding like you.

Step 5: The Newsletter Optimizer (the draft)

By the time I get here, I’m not facing a blank page at all, because I’ve got a locked title, a sharp take, the real proof, and a handful of my own quotes. The draft isn’t starting from scratch, everything it needs I already pulled out of myself.

This is where AI actually writes. The optimizer takes everything I’ve fed in and turns it into a full first draft in my voice. But it doesn’t just spit one out and walk away, it runs me through a short set of questions first, the same ones every week.

It asks the stuff a draft can’t guess: the one real moment this is built on, which of my reader’s worries it speaks to, the line I want her to underline, what I want her to feel, the one small thing she can go do this week. Same questions every time, and after a couple months my own answers basically become my style guide, so the drafts get better because I’m getting clearer, not because the AI is. Then it drafts into a shape that works, and signs off the way I always do.

Build a skill called newsletter-optimizer. Runs with my Council brief and trend
brief in hand. First, interview me with a short fixed set of questions, the same
ones every week: the real anchor moment, the reader-need it serves, the line I
want underlined, the feeling they leave with, the one small action this week,
the tone, anything to avoid.

Then write the full draft in my voice [follow my Voice file], 800 to 1,200 words:
a real relatable moment, a simple no-jargon explanation, why it matters as
opportunity, one small doable action, a reassuring close. Bold the underline
line. End on a question my reader can bring to her dinner table, then my sign-off.
Use only what I gave you. Invent nothing.

What comes back is a real draft, a good one even. It’s just not done, and it’s not mine yet.

Step 6: Take the pen back (the live edits)

This is the part I actually care about, and it’s the part nobody wants to hear takes real time. The optimizer hands me a draft, and I go through the whole thing by hand, out loud, rewriting until every line sounds like me instead of some sharp stranger who read my notes and did their best.

I’ll be straight with you, because people always underestimate this: it’s not a quick polish, it’s a full rewrite, line by line, and it’s the single biggest reason my newsletter sounds like a person. Skip it to save twenty minutes and you’ve wasted everything the steps before it set up.

First I hunt down the AI tells and kill them: the em dashes, every one (nothing screams robot to me faster), the puffed-up words, the neat little groups of three. I keep my own list of words I’d never say, and I run every draft against it.

Then comes the part that actually matters. I read the whole thing out loud, and any line I wouldn’t actually say to a friend at pickup, I rewrite until I would. I put my real details back where it went vague, I add the aside I’d really make, the caveat it was too polished to include. I’m not making it perfect, because perfect is what the draft already was, and that was the problem. I’m making it mine.

Start your own list now, even if it’s just three words, and every draft, notice what you keep changing and add it, so that in a month the draft shows up already half-sounding like you.

Step 7: Publish it, live and ahead

Shortest step, and the one that takes the most discipline: you publish, scheduled and ahead of time, done.

The trap at the end is the same one at the start, the almost-finished draft that sits one more day, then another, until it’s stale and nobody ever read it. So I schedule the send and move on, because a newsletter that goes out on a slightly-off Tuesday beats a perfect one that never ships, every time. Then I start catching breadcrumbs for next week.

What mine actually looks like

My real week looks like this. Monday to Sunday I’m just dropping breadcrumbs, not even thinking about the newsletter. When it’s time, I read the brief over coffee, get my title options, and let the Council interview me for ten minutes, which is still the part that feels like magic, because I sit down sure I’ve got nothing and get up with a take I actually believe. The optimizer drafts it, I spend more time than anywhere else editing it into my voice, and then I schedule it and I’m done.

None of that is me staring at a blank page. I don’t start from nothing anymore, I start from a draft that’s most of the way there, and wrong in exactly the ways I already know how to fix.

Start here

Don’t go build all six skills this week, or you’ll end up with six things you kind of use and none you actually rely on.

Start with the basics: this week, just catch breadcrumbs, out loud, into one note. Next week, add the trend scanner so you’re not starting from nothing, and the week after, add the optimizer so you’ve got a draft to edit. Catch the week, scan, draft, edit, and that alone is a real newsletter going out on a schedule, which is most of the value right there. The hook skill and the Carpool Council take it from good to unmistakably you, and you add those once the rest is a habit.

Build the system, so you’ve got the energy left for the writing.

Save this. Send it to the friend who keeps saying they’re going to start a newsletter and has three dead drafts to prove it.

I’ll see you after carpool.

Danielle

The Year I Went in Circles

For a good part of the past year I spent a lot of it going in circles. It’s not fun to admit it, but it’s true, and it taught me some very valuable lessons that I believe will catapult me forward. For me. Last year and into the start of this year, I told myself I was making progress, because I was busy. I was researching, taking calls, reading everything, looking at deals. But I spent months looking at the wrong kind of business, and even longer going back and forth on whether I wanted to buy something or build something from scratch. I’m still on that path. The difference now is that it’s finally getting clearer, and I very recently put my finger on why.

For most of that year, I wasn’t anchored to anything. For someone who spent 5+ years in tech anchored to scorecards, KPIs, OKRs, EOS rocks (IYKYK), these new waters were unsettling. I was reacting to whatever was loudest that week, saying yes to too many things, and getting pulled in five directions at once. Now that has changed, and it’s not like I magically got more willpower or “figured it out”.

What happened is that I have gotten specific about my future self. Like mapping out the actual person I’m trying to become, and I’m letting her decide what gets my attention. Benjamin Hardy calls this being your future self now, and the core idea is simple but not easy: your future is supposed to drive your present, not the other way around. When you lose sight of the person you’re becoming (or trying to become in my case), every decision turns short-term and scattered. And then you do what I did - circle.

Without a goal, you don’t stop. You circle.

(Source from Be Your Future Self Now by Dr. Benjamin Hardy - highly recommend).

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Starting Got Easy. Focusing Didn’t.

Having goals matters more than ever now - and I hate to say it, but that is in part because of AI. Building has never been easier. I can open Claude and have a plan, a draft, a website in about 15 minutes. Trust me - I built a new website from scratch last week, it really only took me that long. When starting is basically free, starting is no longer enough to set us apart (to be clear - I still VERY much believe in starting over not starting).

Knowing what you’re building toward is what carries weight. For me, I came to realize that my why, my goal, is the fear of regret, in a lot of ways. Regret to never try building something of my own because I decided to stay somewhere that felt safe. That fear is why I left my job. It’s also why I can catch myself now when I’m consuming instead of deciding, three podcasts deep on how to buy a business, another book, another research rabbit hole, all of it feeling like progress while I put off the actual choice. To try the hard thing that doesn’t pay off today.

The Six-Question Filter

What I want to share with you today is the framework that I use (borrowed from Benjamin Hardy’s book - which I highly recommend you read). It is a set of 6 questions that helped me figure out what I want my future self to be, distill it down to 3 priorities, followed by clear actions I can take over the next 12 months to get there. I call it my Future-Self Filter (borrowing from Hardy’s Future Self concept), and it’s the lens I now use any time I say yes to something. That yes may be a new client, a digital course to “learn more”, listening to one more podcast.

Here’s the whole thing in one place. Save this one, and come back to it before your next big yes:

The Future-Self Filter

1. The Priority Question - Who do I want to be, and what few things get me there?

2. The Weed Test - What am I saying yes to that my future self would drop?

3. The Busy Trap - Does this move me toward her, or just keep me busy?

4. The Ask - Am I asking for what I want, out loud?

5. Build vs. Watch - Am I building something real, or watching other people build?

6. Decided or Hoping - Have I decided this is mine, or am I still hoping?

I pulled them from Hardy’s framework, which he actually splits into things to do and traps to avoid, and I kept the six that were key for me. They don’t take long to answer, but I do recommend spending some time with each question. Journaling, writing down points that come to mind. Think of it as six ways to figure out what actually is worth your time. Because time is the one asset you can’t buy back. It’s the most sacred thing we have.

Here they are again, with the raw version of how I’ve been using them, so you can get some context on how it is helping me on this journey.

1. The Priority Question: Who do I actually want to be, and what are the few things that get me there?

(Hardy’s first move: get specific about your future self and your handful of 10x priorities.)

For me the honest answer is my family, my health, and growing businesses for the long term. What I knew was that I wanted to be intentional about carving out meaningful time with my family (including extended family who mostly live abroad), making space for my mental and physical health. And most challenging, realizing that I want to grow businesses for the long term, which means it can be either through building or buying. But recognizing that long term is the goal is what shapes the path.

Naming the few things that actually matter is what makes every question after this one easier. It’s the lens I apply now to how I spend my time, down to something as boring as weekends.

2. The Weed Test: What am I saying yes to that my future self would drop?

(Hardy calls lesser goals the weeds in the garden. They choke the thing you actually planted.)

This is the one I struggle with the most. It is so easy to take on another piece of fractional work or one more client, and the money is real, so it feels responsible. And it’s immediate. But if I’m honest, more of that is not the best use of me right now, not when there’s a bigger picture I’m trying to build. Choosing the craft over the easy option is not comfortable. It’s just the aligned call, and I have to make it on purpose. What helps me is thinking about work as the craft, not just a job. If an action or commitment helps me improve the craft, then it is worth my time. If it doesn’t and it conflicts with my priorities, then it doesn’t deserve my time.

3. The Busy Trap: Does this move me toward future me, or just keep me busy?

(Hardy’s rule: important before urgent. The trap he names is letting small, urgent goals run the whole day.)

Busy is progress’s best disguise. For a while I was pushing hard on Instagram, telling myself it was how I’d get into public speaking. It wasn’t aligned, and it wasn’t even the right room for me. What actually worked looked completely different: I’ve been on four podcasts in the last two months, and I enjoy it more than anything I forced. There are many paths to the same goal, and part of this filter is noticing when you’re grinding on a busy one instead of a real one.

(Source from Be Your Future Self Now by Dr. Benjamin Hardy - highly recommend).

4. The Ask: Am I asking for what I want, out loud?

(This is one of Hardy’s seven steps, and it’s the one most of us skip, myself included.)

This is where the arena stops being a metaphor. I started something I call my 100-person list, reaching out to more than a hundred people over a couple of months, people I’ve never met and people I hadn’t talked to in years. Plenty of it goes nowhere. I also take the calls and make the introductions when there’s nothing in it for me, because being in the arena matters. And really, paying it forward is just the right thing to do. Gary Vaynerchuk has a line that I love - that you should attach your confidence to your intentions, not your abilities or your results. Asking out loud is uncomfortable every single time, but those real conversations have been more meaningful for me than anything I’ve ever consumed.

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5. Build vs. Watch: Am I building something real, or just watching other people build?

(Hardy is blunt here: not being in the arena is failing by default. The fix is to ship imperfect work.)

For a long time I watched other people document what they were doing and felt real awe at the guts it took to be that public. Then it clicked that the watching was the problem. I was deep in the Acquiring Minds podcast while I hunted for a business, stacks of books, endless research, all of it real information but no action. Making something that can actually fail or be judged, writing this newsletter, building the workflows, is the arena.

And the odds of succeeding are shifting toward the builder: so much of what’s online now is machine-made, a majority of long-form LinkedIn posts by recent estimates, that a real person who shows you what they actually built has become rare and worth trusting. As Hardy puts it, the longer you wait to enter your arena, the more you limit your future self. So I am applying this concept by focusing on bias towards action - getting out there, doing the thing, failing, getting back up and improving on the next round.

6. Decided or Hoping: Have I decided this is mine, or am I still hoping?

(Hardy’s progression: you move from needing, to wanting, to knowing. Knowing is when you act like it’s already yours.)

For most of last year, I was hoping. I wanted the future self but wasn’t sure what that should look like. I hadn’t truly sat down to think about my priorities and how to align them with my actions. So I stayed busy and sometimes unfocused and, yes, going in circles. Now I have actual goals I can march toward and something to hold myself accountable to, and the difference in how I make decisions is night and day. This is the turn from wishing your future self into existence to simply being her.

Try This Before Your Next Big Move

So here’s the one thing to try this week. If you are trying to figure out a big decision, or want to test out what your future self could look like, walk it through the six questions. What you should come out with is 3 priorities and tangible ways to achieve them in the next 12 months. Hardy’s full framework is more in depth, and if you do have the time for 14 questions, then its worth the time. If not, stick with the 6 I highlighted.

If you want to go a layer deeper, paste this into Claude and let it interview you (using Wisrp Flo/talking):

“Interview me as my 20-year-from-now self who is living the life I actually want. Ask me the six questions one at a time (priorities, what to drop, busy vs. aligned, what I’m not asking for, building vs. consuming, deciding vs. hoping), then tell me what that version of me would choose about [your decision], and why.”

A Few Steps Ahead, Not Above

If you’ve read this far, you probably found yourself somewhere in here, the circling, the busy that felt like progress, the research that was really avoidance. I’m not muhc further ahead. As I am writing this, it is from about a step ahead, still catching myself, still running my own filter most weeks. The fact that you’re thinking about the person you’re becoming at all means you’re already doing the part that compounds.

I’m working on the deeper version of this, the actual planning system behind these six questions, the monthly and yearly setup with a two-minute daily check-in that turns them from a gut-check into something that builds over time. The filter helps you find your priorities while the system helps you keep them. If anyone knows me, they know I love a good habit stack. Stay tuned for the guide.

I’ll see you after carpool.

Danielle

And I don’t mean I was daydreaming about it. I was deep in the broker sites, talking to firm owners, meeting with brokers. The whole time I had ChatGPT (because I wasn’t into Claude YET) telling me it was a great fit for me, and it was really wrong.

Some of you already know where this is going.

It’s 10pm, everyone’s finally asleep, and you’ve got the tab open again. You asked it to build you a plan and it built you a really good one. It told you the idea was strong. And somehow you’re sitting in the exact same spot you were sitting in back in January. The plan could be a new job, career pivot, writing a newsletter. You name it.

(This is what "keeping my options open" actually looked like, nothing enters the “done” box).

Last week I gave you six moves and told you to start, and I meant it. But starting was is only part of it, so I owe you the other half of that conversation.

Here’s what this edition is. By the end of it you’ll know the specific way AI can walk you confidently in the wrong direction, why the people who are BEST at learning are the most at risk (which was very fun to find out about myself), and the 3 things I do now so that I actually finish something.

Save this one, especially if you’ve been “looking into” something for a while.

How the analysis walked me into the wrong industry

When I started looking at businesses to buy I had some context, but not much beyond what was traditionally considered a good fit. Recurring revenue, fragmented, non-discretionary, limited customer concentration. The boring stuff. But I wasn’t exactly sure which industries were the right fit. So I did what I always do when I don’t know something. I went and learned.

I spent a good few months on the broker sites. (Which IS the right place to look, by the way. That part wasn’t the mistake.)

And somewhere in there, the analysis walked me straight into accounting firms (plus one or two Acquiring Minds podcasts, IYKYK).

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Every reason checked out. I understood the industry, it was completely remote (great when you have three little kids like me), it was professional services which I know cold, and I really liked the people I’d be working with. I talked to brokers, I looked at real firms, and every time I brought the thesis back to ChatGPT and asked what it thought, I got the same answer, which was that this is a good fit for you.

However, here is where the thesis fell flat. It wasn’t the work that lights me up (zero surprise for anyone who ever worked with me at EY), and if I’m being honest I already knew that. But the bigger problem was the math. The prices were really high (10x multiple anyone?), and when you look at where AI is going, an accounting firm is nowhere near as stable a thing to hold as the analysis made it seem.

It took me way too long to see it.

I used AI to build a beautiful case for buying a business that AI is coming for.

The curve that explains it all

Sahil Bloom wrote a piece back in December called The Energy-Output Curve and it’s been gnawing at me. Go read it, it’s short.

(Image Source - The Energy-Output Curve by Sahil Bloom - highly recommend you read it!)

His idea is that effort and quality don’t move in a straight line, and that the relationship has a shape to it with three parts.

There’s the activation phase at the start, where a small amount of energy gets you a huge jump in quality, and it’s exciting because progress is fast and obvious. (Spinning up a website for fun, anyone?)

Then there’s the valley, the long grinding middle where every extra bit of effort buys you less and less, the work stops being interesting, and the dopamine drops.

And then there’s the final 5%, where quality suddenly surges again. His point is that most people never get there because they quit somewhere in the valley, and he says it’s because they’re staring at the outcome and the outcome has stopped paying them back. (Think Instagram likes and followers just plateau, dopamine drops.)

That’s his framework and I never would have found those words on my own. Also because I am nowhere near as eloquent as him. But there is a part of that journey, that curve, that really feels like mine, and it’s the reason I’m writing this piece.

AI is REALLY good at the activation phase

Think about what a chat window actually does for you and how that is vastly different than a google search.

It gives you that first surge of dopamine, instantly and for free (or a $20 pro subscription), a complete and polished plan in about thirty seconds, and it costs you almost nothing spin up. That’s the activation phase, on tap, all day. That’s scary.

And doesn’t truly prepare you for the valley, which is where all the real work lives, unfortunately for me. The valley is making the calls, sending the emails and LinkedIn DMs nobody answers, being told NO by people you respect (or don’t). AI can’t do any of that for you and it probably won’t (minus automated outreach campaigns, which quasi count as the valley, but for another time).

So here’s what happens to people like me. We hit the valley, it stops feeling good, and instead of pushing through it we quietly go back and run the activation phase again. New thesis, new analysis, new plan. And it feels AMAZING, because that part of the curve always does.

Those months on accounting firms weren’t me being stuck. I was running the activation and truly in the valley too, speaking to brokers, looking at CIMs, getting on calls, connecting with firm owners. It was progress, but it stopped pretty quickly. In part because it was hard but really, because the activation phase got it pretty wrong for me and it took starting in the valley to figure that out.

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The thing I cut, and what happened

Last edition I told you I was doing a little bit on Instagram, that I really didn’t like it, and that I had no idea if I’d stick with it.

I deleted it, and I felt better within minutes.

Thinking back to Sahil’s piece, this is why I think it worked. Instagram was another activation phase (although I really did get learnings on public speaking and stepping out of my comfort zone). But it was truly quick hit, instant feedback. And when I took it away, the hours went somewhere else. I read more, I actually prospected, I did outbound, set meetings, I talked to real people who might become clients, I was told no. And learned where my business model for AI consulting has some REAL flaws.

That’s all valley work. Boring, slow, nobody’s clapping (except me). It’s also the only work that’s ever moved this business and growing process an inch.

Why this is so much worse for people like me

Okay so here’s the part that I feel uncomfortable sharing, but is true.

I’m good at learning. When I worked with a coach that was some of the clearest feedback she gave me, and she meant it as a compliment, and it IS a strength. It’s why I was always the swiss army knife at work, especially in Tech. Something breaks, swoop in, figure out what’s actually wrong, figure out how to fix it, get people who never talk to each other working together. That’s been my whole career. And I’m pretty good at it.

So what happens when you hand a person like that a machine that does cross-functional analysis on steroids, instantly, for free (or semi-subsidized), forever?

You get me, months deep in the wrong industry, with a beautiful thesis and a machine cheering me on. But looking at businesses that were just not the fit.

There’s a Harvard Business School study that’s pretty interesting. Knowledge workers using AI finished tasks 25.1% faster and produced 40% higher quality work, which sounds great, except accuracy dropped 19% the second they trusted it uncritically on the wrong kind of task.

So it made them faster and it made the work better and it also made them more confident about being wrong, and that last part I’m always worried I am vulnerable to.

It agrees with you, and that’s no good

Stanford tested eleven of the big models this March and found they affirm what we’re doing about 49% more often than an actual human would. But the flattery isn’t the scary part, the scary part is what the flattery did to people. The ones who got the agreeable AI ended up more certain they were right and less willing to change course, which is a pretty good recipe for getting stuck, and I was stuck for months.

It’s also a good recipe for ruining critical thinking, and that scares me as a parent, but that’s a whole newsletter for another time.

There’s a newsletter I read this weekend called AI Skill of the Week and they have a name for this that I love. They call it the Yes-Man Loop. You share a plan, the AI says it’s solid, you feel good, and then two weeks later the plan falls apart and nobody ever told you what was wrong with it, including the AI you asked.

Which is why I show up here every week

I write this thing every single week. Some weeks it’s great, some weeks it’s average, and honestly I have no idea which it’s going to be when I sit down and start to brainstorm.

I keep doing it anyway, and it’s less about discipline and more that it’s the only way I can prove to myself that I’m still in the valley and haven’t quietly wandered out of it. This newsletter is my accountability, out in public, where I can’t pretend otherwise.

If you’re building something you probably need your own version of that, some thing you keep doing whether or not it’s working yet.

3 things I do now

None of this is complicated and all of it is free. It’s what I have found to help me prevent the “Yes Man Loop.”

1. Push back on it every single time.

Every session, not just when I remember. I ask some version of these three and I don’t move forward until I have:

• Tell me where the holes are.

• Tell me if you’re telling me what I want to hear.

• Tell me where this doesn’t work.

I can’t even begin to tell you how many times that helped me out.

2. Build the pushback into the tool so you don’t have to remember it.

This is a bit next level, but worth it if you are playing around at all in Claude Cowork or just using Projects in Claude. This past week I built a skill whose whole job is to refuse to agree with me and refuse to sugarcoat anything.

I got the idea from AI Skill of the Week, and their version is free and sitting right there on GitHub, and it’s really good. It runs an assumption audit, it takes your logic apart, it names the actual bias you’re running on (sunk cost, confirmation bias, planning fallacy), and it ends with one uncomfortable question you can’t dodge.

Build your own version around whatever YOU are most likely to lie to yourself about. Mine is built around the fact that I fall in love with an analysis.

3. Decide what you’ll DO with it, and decide when you have to stop.

This is the one I’m struggling with, and candidly found myself not following a few times this week alone. Research has no natural end, it’ll expand to fill every hour you have and feel productive the entire time, and the machine is never going to turn to you and say okay that’s enough, go call someone, go do THE thing.

So before I sit down with it now I write two things down. What action comes out of this, and when I have to close the laptop and go do something in the real world.

Then at the end of every day I write three things I gained that day, usually work but sometimes personal, and three priorities for tomorrow. (I stole this from The Gap and the Gain, by Dan Sullivan and Benjamin Hardy, and it’s one of the only things from a book I’ve actually stuck with.)

Three gains, three priorities. It’s almost embarrassingly simple, and it’s the most useful habit I have because it’s the only thing that shows me I’m getting traction instead of just getting smarter.

So what do we do with this

Start. I still mean it, last week’s six moves still hold.

But go in knowing that the smartest model you’re working with (and crazy to think this AI model is the dumbest it will ever be) has one very specific bias and it’s toward agreeing with you. Use it to think, but don’t use it to decide, and don’t let it be the thing that tells you you’re ready, because it will tell you that every single time. And it will mean it, and it will be wrong. Trust me, I have probably lost what amounts to weeks by using Claude too heavily.

The activation phase is free now and everybody gets access to it because of the models. Which means the the game must move to the valley, and almost nobody is in there, or stays there long enough. Because its HARD.

Save this one. And if you’re the friend who’s been “looking into” something for two years, maybe send it to yourself.

I’ll see you after carpool.

Danielle

Then it happened to me. A LinkedIn connection request came in from someone I’d been following for a while, a guy who spent years living in an RV with his kids while building a really impressive business. He owns a professional services business and launched an AI community to support it, and since he moved into AI a couple of years ago, I’m guessing my posts about the agency were doing their job. Last week I ended with a question about owning something of your own, even something tiny. I didn’t expect to have an answer this fast, and I definitely didn’t expect to be putting a whole guide into words within the week.

So that’s what this edition is. By the end of it you’ll know what I mean by a second act, whether the signs are there that you’re thinking about one, and the 6 moves I’ve actually made over the last year that you can borrow.

Save this guide for the day you need it.

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So what’s a second act?

A second act is the thing you build with everything you’ve already learned one or multiple decades of experience. It might be a business you buy. It might be an agency you build, a newsletter you write, a fractional practice you launch, a community you grow. It doesn’t always mean you have to quit to start, and it can be done even when your evenings are busy with your family.

Here’s why I think so many of us, myself included, have been thinking about a second act or are starting one. People in my network who have spent one, two, even three decades across banking, finance, real estate, tech, corporate, all those classic post-MBA roles, roles with a lot of shiny object syndrome and sometimes golden handcuffs, are starting to ask some version of the same question: how can we have more? And it’s often not more money, but more meaning. We know loyalty to a firm is kinda dead. The data is showing us too. In one 2026 survey of career changers, bad work environments (43%), work-life balance (41%), and purpose (40%) all beat pay (30%) as the reason people made a move. Money came in fourth!

And the timing works in our favor, because starting used to be a lot more expensive than it is now. Remember Microsoft Paint? Paint was just there on the desktop. There were no rules, you’d just open it up and make ugly things. Sometimes friends would use it to make really funny pranks, but mostly we did it because it was there.

AI has now done that for starting our second acts. (People love saying “AI won’t take your job, a person using AI will.” I roll my eyes every time. The interesting part is that AI removed the friction to START.)

(Benefit of working for myself is full WFH flex)

First, how I got here

Two years ago May I went to my 5-year MBA reunion, and I was really nervous going in. I had just had my third kid, he was five months old. I had been promoted to VP at a tech company literally the week before. But these weren’t big, fancy names, right? I had learned a ton over those years because I actually owned a number, but I didn’t have the shiny title or company name to support it. I figured I’d spend the whole night listening to other people’s promotions and their really impressive five-year resume accomplishments.

Boy was I wrong. Person after person told me they were leaving their jobs. They wanted work that was interesting but also let them spend more time on their personal life. Some of them wanted to meet a partner. Some of them wanted to maybe try for their first kid. I drove home feeling like I had actually accomplished so much over those past few years, even though it didn’t feel that way going in. The experience I had underestimated had built a lot of really meaningful skills, while also letting me build a meaningful family life.

I think about that night a lot now that I’m building my second act.

The signs you may be ready for a change

I keep having the same conversation lately with people a couple of decades into their careers. Some are in comfortable jobs. Some already walked away, burnt out, and are figuring out how they want to come back. I’ve had every single one of these myself:

• It’s 10pm, everyone’s asleep, and you’re googling businesses for sale (for those of us who didn’t hear about this in business school, it’s flooding the internet right now)

• You want to build a life where wealth means more than money, it means control of your time, your health and your relationships

• A friend announces their newsletter, their side hustle, or that they’re leaving corporate to build their own business, and you feel a little pang. Happy for them, and a little jealous

• You keep daydreaming about your version. Mine was owning something of my own, even something tiny. Yours might be a newsletter, a small business, a practice with your name on it

• You’ve told exactly one person that you want to build something of your own. Everyone else still knows the corporate version of you

• You have one or two decades of experience but no one-liner yet for what you’d build with it

• Your evenings are dinner, homework, and bedtime, so every plan that assumes free nights makes you laugh

Two or more? This one’s for you.

You’re allowed to find out you don’t want this

One thing before the moves, because it changes how you read them. You do not have to know if you want this yet.

You might fantasize about being on your own, writing a Substack, running a passion Instagram account, buying a small business. The fantasy version only tells you part of the story. Start building a small piece of it and you’ll know pretty quickly. Do you actually enjoy the work? Do you enjoy the lack of structure? Do you like having nobody to report to, or does that turn out to be really hard? Some people test it, learn they love the idea more than the reality, and go back to their job with a completely different level of peace. That is a GREAT outcome.

Wondering for ten years is so much heavier than testing for six weeks. Every move below works even quietly, even tiny, even on the side.

The thing we’re trying to kill here is regret.

Move 1: Take stock of the skills and network you already have

I see the proof in experience and network in the buy-a-business world. Stanford runs a study every year on people searching to buy and run small businesses, and the 2026 one shows a fast-growing share of buyers coming in after 10 to 20 years in industry. I’ve been meeting these searchers in their late 40s and 50s as I explore that space myself, and they’re some of the most focused people I talk to. They know why they’re doing it, they know exactly what kind of business they want, and they have the operating years to actually run it.

So here’s my takeaway. With one or two decades of work behind you, you’ve probably solved a lot of really interesting problems. You’ve run teams. You’ve sometimes had to own a number. And you have a real network of people who would vouch for you. But most of us, myself included, never sat down to write any of it down.

Try this: talk it out. Plop your LinkedIn or your resume into Claude and just get it all out there. Ask it to find the themes and the path you’ve actually built, then to help you identify the people worth talking to, the ones who can tell you where you’re strong and where your industry experience points. Side note - to get the list of people in your LinkedIn - export your list of contacts into a CSV and pop that into Claude. It can surface up the right people to talk to that you may not have thought of.

Move 2: Be realistic about the time you actually have right now

Every playbook I read assumed I had free evenings. I don’t. For me, the building happens in the hours between school drop-off and school pick-up. This move is a mix of finding your hours, being realistic about them, and figuring out where you can squeeze in 15 to 20 minutes to test something.

Here’s what that actually looked like for me. Before I left tech, my version was small and scheduled. I had monthly sessions with a coach, I’d allocate 30 minutes a week to the exercises that helped me figure out what I actually wanted, and an hour a week for calls with people to start exploring. Now that I’m building, I have set times in my day blocked out, and those are the only times I’m allowed to write the newsletter or create any social content, because otherwise I get distracted.

Try this: that might mean 30 minutes a week, say 4:00 to 4:30, where you start inventorying your skills and the industries you’re passionate about. Put it on the calendar and give it one job.

Move 3: Test it where nobody’s watching

You can test it first in a way where people don’t see it.

This newsletter is where I’m quietly testing things out, and it feels a lot safer than blasting things on LinkedIn (I do post there - but its different and less personal). It’s become cathartic, a place to get my experience down while I’m in the middle of the journey instead of after. Building can be lonely, and this is how I share what I’m doing with people. There’s also a reason I didn’t expect to care about so much: it’s documentation. Someday my kids can come back here and see who I was and what I was building while they were little.

I know I’m not the only one, because Substack paid subscriptions grew 67% year over year. I think part of the reason is that it’s long-form, it’s an audience you can own, and you don’t have to have people from your professional life peeking in or evaluating it until you’re ready to share. Most people aren’t looking up your name on Substack right now, and that’s a good thing, because it helps you stay a little more private while you figure out what this looks like.

I’m also doing a little bit on Instagram right now, and I really don’t like it. The only reason I’m doing it is I know I’m not a great public speaker, and it forces me to practice that skill. I really don’t know if it’s something I’ll stick with.

A friend of mine is in the middle of a move and decided to take a corporate pause, and when we caught up she told me a lot of her friends are doing something similar. I did something similar when I left tech before trying to start my own thing. I took two months off, read a ton, journaled, and tried to prioritize, and it was really helpful. What I will say is that until I actually dug in and started looking at businesses, that’s when I really started to form an opinion and understand if my why still held.

Try this: pick your lab. A newsletter, a workshop for five friends, one fractional project. Give it six weeks before you judge it.

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Move 4: Just get started (ugly counts)

Back to Paint. Nobody was qualified, it was just there on the desktop, so we made ugly things and learned.

Here’s mine. In December the fear of posting on LinkedIn was very real, so I let AI write my first posts just to get me over the hump. The posts went up, nothing bad happened, and after enough reps the fear wore off. Now I write everything from scratch.

For me, building in public has opened up really interesting conversations, but I had to start. The RV guy found my content because I was posting, and a year of me quietly following him turned into an actual conversation. Another friend of mine went fractional for a while, went back into tech, is doing really well there, and she still asks, is this really it? I love that she’s being honest about that.

Try this: do one ugly thing this week. A post, a one-page website, a note or an email or a LinkedIn DM to someone you admire. Ugly and done beats perfect and drafted.

Move 5: Keep collecting, the dots connect later

If you’ve tried any of the moves above, you might already have two or three little things going that don’t obviously match. Same here. For most of this year I would have told you I was juggling three different things. An AI agency. A personal brand. A search for a business to buy. Some weeks it felt slightly unhinged. Then it clicked. AI is the thing that connects all of it. It’s helping me build my brand. It’s making my search smarter, because I’m learning which industries will or won’t get disrupted and where AI can help a business operate better. And the agency is where I’m learning how to actually put those skills to work inside a business. It all really comes together, and I get to document the whole thing in one place.

I keep seeing the pattern in other people too. A banker I met interviewed 450+ CEOs as a passion project. He built his own business before that, and he just kept the interviews going, no master plan. The network is huge, and it’s brought him some really interesting banking opportunities. He made those connections over years, and now they’re naturally starting to build out opportunities for himself and his network.

Try this: ask the three people who know your work best, “what would you come to me for?” The overlap is your answer.

Move 6: Stop building alone

Building can get lonely, and my answer is a bench. A few humans who get it, plus a small stack of AI helpers doing jobs I could never hire for this early: one agent scans trends for me, one edits my writing, one is building out my marketing and website. That used to be three separate hires, now it runs for one person with no funding.

The humans matter more though, and the ones I keep close are living proof that none of this is linear. One guy I know worked in venture capital for years, went looking for a business to buy, and ended up launching his own agency working with startups instead. He loves the work and finds real meaning in it, and he’d tell you the detour WAS the process, you test things until you find where you want to land. One of the most impressive women I know was very senior at a top-tier consulting firm and left to build a business helping women in corporate manage the mental load. Another spent years in tech and is now building a community around AI for moms while doing serious consulting work in the VC and private equity world. Second acts often flourish because of the bench you built over years.

Try this: start to list out your bench and connect with people in your network who are doing interesting things. Those on their own second acts. Set up monthly check-ins to learn, share progress, lament. Best therapy session there is.

Save this for the day you’re ready

The old deal, the one where you stayed loyal to a company and it took care of you, came apart quietly. I keep thinking we got something better in the trade: the chance to build a more meaningful life on our own terms. Remote work was a really good step in changing how we work. AI is now another step, giving us the ability to build, and even something as simple as flexible hours or working from home a little is one really tangible way to take advantage of it.

Building can be lonely, which is exactly why I’m documenting mine here, wins, setbacks, and the no’s included. Save this one, or send it to the friend who keeps telling you about the thing they want to start. And if you’re already moving, hit reply and tell me which move you’re on.

I’ll see you after carpool.

Danielle

You don’t need a bigger team. You need a Chief of Staff.

Guide 2: turn Claude into the chief of staff you can’t afford to hire.

I run an AI agency full time, and I write this newsletter for fun. No team, no assistant, no chief of staff, because who hires a chief of staff for a company of one?

For a while my whole system was a to-do list I kept rewriting. I tried blocking my whole calendar like everyone tells you to, and it didn’t work. The blocks didn’t know that the thing due today was actually the thing on fire, so I’d blow right through them and still miss stuff that had to get done. Then I’d be at school pickup with my kids, half there, suddenly remembering the email I never sent. Busy and behind at the same time. You know the feeling.

Here’s what changed. I stopped trying to be more disciplined and built a chief of staff inside Claude. I’ve been running it a few weeks and it honestly feels like a cloud lifted. I start the day knowing what actually matters and in what order, and the small stuff sits at the bottom where it belongs.

This guide is how I built it. The real setup, the actual prompts, and the spots where it’s still a little duct-taped. It runs on the second brain from Guide 1, so it already knows your company, your role, and how you sound. You’re just teaching it to run your days.

(New here? Build your second brain first, that’s Guide 1. This one assumes you’ve got it.)

First, give it a name

Sounds silly. Do it anyway. Mine is Claudia. A name is the difference between a tool you forget to open and a person you actually check in with, morning and night. You talk to a name. You build a habit around a name. You’ll catch yourself thinking “did I tell Claudia yet,” and that little bit of pretend is what makes it stick.

Pick whatever you want, Claudia, Jack, Otto, your kid’s imaginary friend. I’ll say Claudia. You swap in yours.

It’s really just one loop

Forget the fancy chief-of-staff org chart. It comes down to two moves, every day.

Morning, a brief: here’s your day, ranked, with where to actually spend your time. Evening, a brain dump: you tell Claudia what happened, she sorts it, and she remembers it for tomorrow.

The morning brief is only good because last night’s dump fed it. Skip the dump for a few days and it goes stale. Keep it up and it sharpens every morning, because it knows more about your actual life. Everything else in this guide just serves that loop.

Where she lives

One thing to clear up before we build: Claudia is a Project. That’s it. Doesn’t matter if you work in the browser or the Cowork desktop app, it’s the same thing, a project that exists just for this. Everything below goes inside it.

Step 1: Build the Claudia project (15 min)

Make a new project called “Claudia.” This holds the standing context a good chief of staff keeps in their head. Build it the way you built your brain, by talking.

Help me build the standing context for my chief of staff, Claudia. She sits on top
of my second brain, so don't re-cover my company or role. This is about what I'm
carrying right now.

Interview me with the AskUserQuestion tool, in small batches. I'll answer out loud.

Cover:
- My priorities and goals this quarter.
- The people who matter (boss, team, key clients) and what each needs from me.
- My recurring meetings and what each is really for.
- The live projects I'm driving, and where each one stands.
- What tends to slip through the cracks for me.

Then write a tight standing context I can save as Claudia's instructions, plus a
starter Open Threads list. Keep it lean, I'll update it as we go.

Save it as Claudia’s instructions. This is the one thing you’ll refresh often, usually on a Monday.

Step 2: Give Claudia eyes (the connectors)

A chief of staff who can’t see your calendar is guessing. This is the step people skip, then wonder why the brief feels generic. Turn on the connectors so she works off your real day.

The two you actually need: Calendar for the brief and meeting context, and Email for triaging what comes in and sending the follow-ups.

• Google (Calendar + Gmail) is the simplest, and it’s what I use.

• Outlook works too, through the Microsoft 365 connector. Two honest catches: it’s read-only (Claudia can read and draft but not send), and it needs a work Microsoft account, not a personal @outlook.com. There’s also a Claude for Outlook add-in in beta if you want more.

To turn them on: Settings, Connectors, switch on Calendar and Email, approve the pop-up. On a personal plan that’s two clicks. On Team or Enterprise, some are admin-controlled, so if a toggle is greyed out that’s a policy setting, not you, and a quick note to IT usually fixes it.

Point her at your running agendas too. This is the one that made the biggest difference for me. I keep running agendas for my meetings and projects, and Claudia reads them, so the brief knows what’s actually coming, not just what’s on the calendar. Connect wherever they live (Notion, Google Docs) or drop them in the project.

No connectors at all? You’re not stuck. Paste in your agenda and forward yourself the emails you want handled. Connectors make it automatic, pasting makes it work today.

Step 3: Give her a memory (a running doc)

This is the piece that makes the loop build on itself, and the one most setups skip. Here’s the trap: if you just talk your day into a chat, that chat is a dead end. Tomorrow’s brief opens a fresh conversation that remembers nothing. The dump has to land somewhere it sticks.

So point Claudia at a running notes doc. Each night your brain dump gets added to it, dated. Each morning the brief reads it. That doc is your memory, and it’s the answer to “where does my voice note go.” Straight into the doc.

I keep mine in Notion, a page called “Claudia EOD Brain Dumps.” Could be a Google Doc, a Notion page, whatever you already live in. Set this up now, before the skills, because the skills read and write to it.

Step 4: Build the two loop skills

Same move as Guide 1: tell Claude what you want, let it build the skill, run it with /. These two are the whole loop.

1. Daily Brief · /daily-brief Your whole day, ranked, in 60 seconds.

Build a skill called daily-brief. When it runs in the morning, read my Claudia standing context, my running notes (last night’s brain dump), my running agendas, and today’s calendar. Then give me: a two-line context up top (what I got done yesterday, and what kind of day today is), a “Where to focus today” section with the 2 or 3 things that actually matter and why, a “Today’s to-dos” list matched to my brain dump, most important first, marking anything already handled and flagging anything you couldn’t find in my calendar or email so I know it’s on me to pull up, a “Follow-ups owed” section for who I owe and what, and a callout for any calendar changes like freed-up time or cancellations. Keep it to one screen.

2. Brain Dump · /brain-dump The evening sweep, the one that matters most.

Build a skill called brain-dump. At the end of the day, ask me what happened, and I’ll talk it out. Turn my ramble into what I committed to and to whom, who I’m waiting on, and what’s starting to slip, sorted by area (mine are Numeriq, AI After Carpool, and Personal). Add today’s summary to my running notes doc, dated, and don’t overwrite what’s already there. Then draft the follow-ups I owe in my voice and ask me which to send.

Get the brief without lifting a finger. This is the good part. Ask Claude to schedule it: “Every weekday at 7am, run my daily brief and have it ready for me.” Now it’s just there when you sit down, which is the whole point. You can still run /daily-brief yourself anytime you want a fresh one. (Honest catch: a scheduled run fires while Claude is running for you, so keep that in mind if you close everything down overnight.)

Make the brain dump impossible to forget

The dump is easy, you just talk. Remembering to do it is the hard part. So don’t leave it to willpower, make it a standing appointment.

1. Set a repeating calendar hold. A real recurring event, every weekday, end of day. Mine’s at 5:00pm, called “Brain dump to Claudia.” Set it to repeat and forget about it.

2. When it goes off, don’t type, talk. Open Claudia and talk it out loud, like you’re catching a colleague up on the way to the parking lot: who you met, what you said yes to, what’s nagging you.

3. Run /brain-dump. She sorts it, writes it to your notes doc, and drafts what you owe.

Two minutes, before you close the laptop. (Not at your desk? Talk it into the Claude app on your phone.)

Sending: don’t let it sit in drafts

Everyone’s gripe with AI assistants is that they write the email and leave it in a drafts folder you never open. We’re not doing that. But handing over the send button is where you go slow. So, two rungs.

Rung 1: draft, you glance, you send (start here). Claudia writes it, shows you in the chat, you say “send it,” done. No drafts graveyard, no forgetting. This is the default, and honestly where I still am. I keep everything on draft and send it myself. No rush to move off this rung.

Rung 2: auto-send the routine stuff (once you trust her). After a couple weeks you’ll spot the emails you never edit, the got-it-thanks replies, the standard recap, the FYI forward. Tell her: for plain confirmations and recaps, just send them and tell me what went out, and show me anything sensitive first. Now the boring 80% sends itself.

One caveat so nothing surprises you: hands-off sending needs a send-enabled email connector. Some (like the Microsoft 365 one) are read-and-draft only, so there Rung 1 is your ceiling. Still beats a graveyard of drafts.

A quick word on staying safe

If you’re on a Claude Team or Enterprise account, your work stays out of model training by default, so you can put real work context into Claudia and sleep fine. Still follow your own company’s policy. On a personal plan you can turn training off yourself under Settings, Privacy. Either way, use the same judgment you’d use writing a normal work email, and you’re good.

When you’re ready: two more skills

The loop is the whole game. Once it’s second nature, a chief of staff does two more jobs worth automating. Build them the same way. No rush though. Build all four on day one and you’ll have four things you half-use instead of one loop you actually live by.

Meeting Prep · /meeting-prep

Before a meeting, ask me who it’s with and the topic (or read the invite). Give me who they are and our history, the context I need, the one outcome to push for, and three sharp questions to ask. Short enough to read in the elevator.

Inbox Triage · /inbox-triage

Read my inbox and sort it into four buckets: needs a reply, needs a decision, FYI, and can wait. Draft the quick replies in my voice and let me approve each one to send, don’t leave them sitting in drafts.

What mine actually looks like

Enough talk, here’s my real morning brief. I stripped out the details, so what you’re seeing is the structure Claudia gives me every day: a quick context line up top, where to focus, my to-dos matched to last night’s dump (with the done ones crossed off and the ones she couldn’t find flagged), and follow-ups I owe.

Yours won’t look polished. It’ll look like an assistant who actually remembers what you told her yesterday, which is the whole thing.

Start here

Don’t build all of it. Build the loop. Set up your Claudia, point her at a notes doc and your calendar, and make just /daily-brief and /brain-dump. Run them for a week, brief in the morning, dump at 5:00. That pair alone is 80% of it, and it’s the part that lifts the cloud.

Save this. Send it to the friend who keeps saying they need an assistant and has one sitting unopened on their laptop.

I’ll see you after carpool.

Danielle

Here’s how it usually goes.

Your company rolls out Claude. There’s maybe a training, maybe just a Slack message with a login and a cheerful “go explore.” You open it between two meetings, type “write a follow-up to the client,” and get back something fine. Generic, but fine. You tweak it, you send it, you close the tab. Three weeks later you’re still using a tool that could rewrite your entire job like a slightly fancier search bar.

That’s not on you. Claude showed up knowing nothing about your company, your role, or how you sound, so it wrote for the average person doing the average version of your job. You never told it who it was working for.

Here’s the trade: a little focused time up front, and every task after that comes back in your voice, aimed at your world. People give it fancy names. I’ll call it what it is: your second brain. Here’s exactly how to build one, then how to build Skills that run whole jobs on top of it.

Part 1: Build the brain

What a second brain actually is

It’s a small, reusable set of context about you and your work that Claude reads before it does anything, so it stops guessing and starts sounding like it actually works with you. Build it once. Everything you make after that starts from it.

Same idea my other company, Numeriq Advisors, installs for whole businesses: one “AI Brain” that holds how the best people work and feeds every function. This is the personal version. One person, one afternoon.

Why this is the whole ballgame

Once the brain exists, everything you make gets sharper, because Claude finally has the context it was missing.

The same ten-word request (“draft the board update”) now comes back in your voice, aimed at your board, using your numbers, and you didn’t write a single instruction to get there. The people getting scary-good work out of Claude aren’t writing better prompts. They just did this part first.

Engine vs. storage (the thing that trips everyone up)

One idea saves a lot of confusion. People mix up how Claude works with where your brain lives. Two different things.

The engine is how Claude works. Chat is quick back-and-forth. Cowork is the heavy engine that runs long, multi-step work on your files. It’s optional, and your admin decides whether you have it.

The storage is where your brain lives, and it’s the part that matters:

• A Project holds your real second brain (your company, role, voice, and collateral). It’s yours by default, and it’s the one thing you can share with your team.

• Personal Preferences is a tiny always-on note about how you like to work, riding along in every chat.

The freeing part: your brain lives in a Project plus that short note, not in some special mode. So it works the same on Pro, Team, or Enterprise, with or without Cowork. Cowork is just a stronger engine you can point at the same brain later.

If you’re using Cowork

If your company gave you the Cowork desktop app and that’s where you’re working, everything here still holds — same three files, same brain. The only thing that changes is where the files live.

Cowork works from a folder on your computer, not from a Project’s knowledge base in the browser. So in Cowork, your brain is a real folder (call it “My Work Brain”) with your three files saved inside it as plain documents, plus your collateral (brand, templates, a couple of finished pieces) dropped in as files. Point Cowork at that folder and it reads them the same way the browser reads a Project.

Two things to know so you don’t get tripped up:

• Build the three files once, keep the master copies somewhere you control. Paste them into a browser Project when you’re on the web; keep them in your Cowork folder when you’re on the desktop. They don’t sync on their own — you’re keeping two homes for the same files.

• Your always-on note lives in Settings and rides along in both places, so you only write it once (Step 2).

So when you hit “Make your Project” below, a Cowork-only reader can make a folder instead. The interviews, the files, and the test are identical either way.

Your brain is three files

Don’t overbuild this. The brain is three short pieces of writing, and they all live in your Project:

1. My Company. What your company does, how it wins, who it serves, the brand and tone, the goals this year. True no matter who holds your job.

2. My Role. What you own, your day-to-day, who you answer to, what you’re measured on. Your specific seat.

3. My Voice. How you write and sound, plus the AI clichés you never want going out with your name on them.

You’ll build all three by talking, not typing. Here’s the whole thing, in order.

Step 1: Open Claude and Wispr Flow (5 min)

Claude. The browser works fine for all of this. If your company also gave you the desktop app with a Cowork tab, great, but you don’t need it to build your brain.

Wispr Flow. This is the part most people skip, and it’s the part that makes the whole thing work when you’re busy. Wispr Flow is a dictation tool: hold one key, talk, and your words show up wherever your cursor is. The free tier is plenty.

Why it matters: the setup below works by Claude interviewing you, and good answers are the whole point. You talk at about 150 words a minute. You type at maybe 40 (and if you’re me, half of those are typos). You also think differently out loud. You ramble, you give the real example, you say the thing you’d never bother typing. That mess is what makes your brain sound like you. Install it first, then talk your answers.

Can’t install it, because your work laptop is locked down? No problem. Type your answers instead, and just make them long and specific. Talking is the easy mode here, not a requirement. Don’t let a missing app stop you from building the brain.

Step 2: Set your always-on note (2 min)

Open Settings, go to your Profile, and find the box that asks what Claude should keep in mind about you. This note rides into every chat, so keep it short and lane-neutral. It’s your working style, not your company. Paste something like:

Be concise and direct. Skip the preamble and filler.
If a request is unclear, ask me one or two sharp questions before you start. Don't guess.
Use plain language, no corporate buzzwords.
When you write in my voice, follow the My Voice file in my project.

That last line is the trick: your actual voice lives in the Project (Step 4), and this note just points to it. Keep company-specific detail out of here, because this note also shows up in your personal chats.

Step 3: Make your Project (2 min)

In the left sidebar, click Projects, then New project. Name it something like “My Work Brain.” You’ll see two boxes: instructions (always loaded) and a knowledge base (files it pulls from when relevant). That’s where the three files go next.

No local folder to build or maintain. And because a Project is a normal feature on every paid plan, you can set this up yourself even if IT has locked down everything else.

Step 4: Build the three files (10-15 min each)

Open a normal chat and paste one prompt at a time. Each runs a short interview: Claude asks, you talk, it writes the file. Then you drop the result into your Project. Do them in order. Break between them if you need to.

Prompt 1: My Company

Help me write the "My Company" page of my Claude second brain. It lives in my
Project and loads before every task, so keep it short and useful — under a page.

Don't write anything yet. Interview me first. Ask me three or four plain
questions at a time, then wait for my answers before the next batch. I'll answer
out loud, so I might ramble — pull out what matters and leave the rest.

Ask me things like:
- If you had to explain what we do to a smart twelve-year-old, what would you say?
- What do people actually pay us for?
- Who is our best-fit customer, and what keeps them up at night?
- When someone picks us over the other option, why do they say yes?
- If our company were a person, how would it talk?
- What is the one big thing we're trying to pull off this year?

If an answer comes out fuzzy, ask me for a real example instead of moving on.
Never fill a gap by guessing — ask me.

When you have enough, write the page: plain sentences, a few short lists, no
filler and no buzzwords. Then give me two versions — a four-to-five-line summary
to paste into my Project instructions, and the full page to save as a knowledge
file.

Tip: paste your company website link into the chat so Claude can pull from it while it interviews you.

Prompt 2: My Role

Now help me write the "My Role" page of the same second brain. The company page
already covers the company — don't repeat any of it. This one is only about my job.

Same as before: interview me first. Ask three or four simple questions at a time
and wait for my answers. I'll talk it through, so listen for what matters.

Ask me things like:
- What's your job title, and what does that actually mean day to day?
- What lands on your desk that really only you can handle?
- Who do you work with most, and who do you report to?
- How does your boss decide whether you had a good month?
- What do you end up making again and again — the same reports, emails, or docs?
- When you hand something off, how do you know it's actually good?

If an answer is vague, ask me for the specific real example. Ask, don't assume.

Then write the page: tight, mostly short lists, under a page. Give me the
four-to-five-line summary for my Project instructions and the full page to save.

Prompt 3: My Voice (spend the most time here)

This is the file that stops Claude sounding like a stranger who skimmed your LinkedIn once. It has Claude study your actual writing, not just ask about it.

Now the most important page: "My Voice." This is what makes Claude write like me
instead of like a robot. Take your time here.

First, learn how I write. Ask me to paste in three things I wrote and liked — an
email, a text, a note, a post, anything real. Read them and tell me what you
notice, with proof from the samples: how long my sentences run, how formal or
loose I am, the words I reach for, how I start, how I sign off, how I handle bad
news. Don't flatter me. Just tell me what's actually there.

Then ask me a few simple questions, a few at a time:
- Who am I usually writing to, and how do I want them to feel?
- Am I more buttoned-up or more casual? Does it change with who I'm writing to?
- Any words or phrases that feel like me?
- Any words or phrases that make me cringe?
- If a coworker read something with no name on it, what would tell them it's mine?

Then write the page in three parts:

1. How I sound — a real description in my own style, pulled from my samples and
answers. Include the three-to-five moves I make every time, and a plain do / don't
list. Be specific, not generic.

2. Words to never use — the AI giveaways to keep out of my writing. Start with
these and let me add my own:
- the "it's not X, it's Y" flip, in all its forms
- puffed-up words: leverage, delve, unlock, tapestry, robust, seamless, elevate,
  game-changer, and their cousins
- the tidy group-of-three ("faster, smarter, better")
- tired openers: "In today's world...", "It's worth noting that..."
- long dashes stacked in one sentence, and every line the same length

3. Before and after — two quick rewrites that take a stiff, generic line and turn
it into how I'd actually say it, so future-me and Claude can see the difference.

Keep it to about a page and a half. Give me the short version for my Project
instructions and the full version to save as a knowledge file.

Step 5: Feed it your real work (5 min)

The three files describe your world. Your collateral shows it. Upload the real material into your Project’s knowledge base, and your output stops being about your company and starts looking like it came from it: your brand (logos, exact colors, style guide), your templates (a board deck, a proposal, the monthly report), and two or three finished pieces you were proud of, so Claude knows the bar.

Then point Claude at them: “Draft the Q3 board deck. Match the template and colors in this project’s knowledge.”

Step 6: Test it (2 min)

Open a fresh chat inside your Project and ask for something real, with no instructions: “Draft my weekly update to my manager.” If the brain’s working, it comes back in your voice, aimed at the right person, using your priorities. If something’s off, open the one file that got it wrong and fix that file. That’s the whole maintenance loop.

When the test comes back wrong

The first try usually isn’t perfect, and that’s fine. Almost every miss traces back to one file. Match the symptom to the fix:

• Still sounds generic or stiff → your My Voice file is too thin. Add real writing samples and specific do’s and don’ts, not adjectives.

• It made up a number, name, or quote → it’s missing your real material. Upload the actual document into your knowledge and tell it to use only what’s there.

• Too long, or too formal → say so in My Voice, add a “keep it short” line, and give it one before-and-after example.

• Describes your company but doesn’t feel like it came from you → that’s a My Role gap. Spell out what you own and who you’re writing for.

• Ignored your template or brand colors → point it straight at the file: “match the template and colors in this project’s knowledge.”

Fix the one file, run the same test again, and move on. You’re not chasing perfect — you’re chasing “sounds like me, mostly.” That’s the file doing its job.

Skip these four mistakes

1. Dumping confidential data. Keep it to what you’d already put in a normal email. No client data, no secrets, unless your company’s policy clearly allows it.

2. Ten-page files. If a file gets bloated, Claude skims it instead of reading it. Lean or it stops working.

3. Company voice in the always-on note. Personal Preferences applies everywhere, including your personal chats. Keep the company and role stuff in the Project.

4. Giving short answers. Short answers make a generic brain. However you answer, go long and give the real example — that’s what makes it sound like you, not whether you typed or talked.

Don’t overload it

More context isn’t always better. A tight brain makes Claude sharp. A bloated one makes it repetitive, because it leans on the same loaded material for every answer. Fine when you want the same board deck every quarter. A problem when you want it to think with you on something new.

Keep the always-on layers lean, and pull in heavy collateral only when the task calls for it.

The corporate stuff (30 seconds)

Greyed-out buttons? If Cowork, a connector, or a setting is missing, that’s your admin, not you. The Project path here needs none of it.

Your data? On Team or Enterprise, your company’s setup generally keeps your work out of model training, so you can add your work context with reasonable confidence (still follow your own policy). On a personal Pro account, you can turn training off yourself under Settings → Privacy.

Keep it fresh

Your job changes, your goals move, new AI clichés start driving you up the wall. Once a quarter, spend ten minutes rereading your three files. Cut what’s stale, update this year’s goals, add new phrases to the banned list, swap in a fresher writing sample. A brain you never update ages like milk.

Reuse it across Projects

The moment you spin up a second Project (a client, a launch, a new team), you’ll want the same you inside it. Here’s the rule that trips people up: a Project’s files stay in that Project. They don’t sync.

So keep your three About Me files saved somewhere central, and re-drop them into each new Project’s knowledge base, with the short summary pasted into its instructions. Then add only what’s specific to that project on top. Your Personal Preferences already ride along everywhere, so the light layer is automatic. Build the About Me once, and stamp it into every new workspace.

Part 2: Turn your brain into Skills

You built the brain. Now stop re-explaining the same tasks.

A Skill is a saved capability you trigger with a slash command, for the work you do again and again. Your brain tells Claude who you are. A Skill tells it how to do a specific job the way you like it, every time, without re-explaining. And because the Skill runs on top of your second brain, it already knows your voice, your brand, and your numbers.

Where Skills live

Two places. You fire a Skill by typing / in any chat and picking it from the menu. You manage them (create, edit, turn on and off) under Customize → Skills. If you don’t see Customize, your company may have it switched off. You can still keep a Skill’s instructions in a note and paste them when you need them.

How to make one

You don’t write code. You describe what you want, out loud, and Claude builds it.

Two ways in:

1. Run /skill-creator and talk it through (Wispr Flow again). Tell it what the skill should do, what to ask you for, and what “good” looks like.

2. Save a win. Any time Claude nails a task, say “save this as a skill.” It turns that chat into a reusable command.

The whole trick is the description. You’re not programming. You’re briefing a sharp assistant on a job you want done the same way every time.

Four skills worth building first

Here’s what each one does, and the plain-language brief you’d hand /skill-creator to build it. Swap in your own details.

1. Friday Recap Email · /friday-recap Turns your week into a polished recap email to your boss.

Build a skill called friday-recap. When I run it, ask me what I worked on this week: wins, what moved forward, anything that slipped, and what’s next. Then write a tight recap email to my manager in my voice (follow my Voice file): a one-line summary up top, then wins, in-progress, and next week, with any blockers flagged. Keep it skimmable. Only use what I actually gave you, don’t inflate.

2. Friday End-of-Day Recap · /eod-recap A quick, informal end-of-week wrap-up for you or your team.

Build a skill called eod-recap. When I run it, ask how the week went and what I got done. Then give me a short, casual end-of-day recap I can drop in Slack or keep for myself: what shipped, what’s still open, and where I’m picking up Monday. Loose and human, not a formal report. Same facts as my boss recap, lighter tone.

3. Content Creation Engine · /content-engine Drafts posts in your voice, and a first-draft press release when you need one.

Build a skill called content-engine. When I run it, ask what I want to make (a social post, or a PR / press release draft), what happened, and who it’s for. For a post: draft it in my voice (follow my Voice file), lead with a real hook, keep it tight, give me two versions. For a PR draft: use my company’s tone from my project, with a headline, a strong first paragraph, a quote slot, and a boilerplate at the end. Only the facts I gave you, don’t invent numbers or quotes.

4. Recurring Meeting Agenda · /meeting-agenda Builds the agenda for your recurring meeting, in your format, every time.

Build a skill called meeting-agenda. When I run it, ask which meeting it’s for, who’s attending, and what’s on my plate this week. Then build the agenda in my usual format: carry over open items from last time, group by topic, and leave space for notes and action items. Keep it tight enough to actually get through. Match how I run that meeting.

The rest of the menu (build these the same way when you need them): /meeting-prep, /board-update, /exec-summary, /competitor-onepager, /email-reply. Same move every time: describe what you want, let Claude build it, trigger it with /.

One rule: start with one. Pick the task you do most, build that skill, use it for a week. Then add the next.

Your next moves

Take one sitting this week and build the brain: Steps 1 through 4 (through your first file) together, My Role and My Voice on two more short breaks, then feed it your collateral and test it. A working second brain by Friday. Then build one Skill, the task you do most, and watch a week of that job get shorter.

That’s the system: a brain that knows you, and Skills that run your repeat work on top of it. Next time I’ll show you how to stack Skills into full workflows, and how a team can share one brain instead of everyone building their own.

Save this. Send it to the colleague whose company just gave them Claude and who still hasn’t opened it.

I’ll see you after carpool.

AI After Carpool · Build your second brain

(real snapshot of an RV spotted on our Colorado roadtrip circa 2018)

The daydream I can’t shut off

My husband floated something a few months ago that I couldn’t take seriously at first. What if we rented an RV for four months and took the kids when they’re a little older? My honest first reaction was, that’s insane. How do you work like that? The kids need to be in school.

But it stuck. And then I read about this woman on someone’s Substack who basically does this for a living. She coordinates summer trips overseas, places like Spain and Italy, where the kids go to camp during US working hours, surrounded by kids from all over the world, this whole multicultural thing, and you get to actually be in Italy while you work. I read it twice. It pulled me right back to our honeymoon, this unbelievable little winery we still talk about (keep reading for pic of said winery).

A few weeks ago I watched a pile of kids (mine + a family friends) on a beach, all different ages, no devices anywhere, just figure out how to play for hours. Sand, water, each other. Bored enough to get interesting. And I thought, that. I want more of that. Maybe the whole point was never more stuff. Maybe it’s more of that.

I did not expect a half-baked RV fantasy to crash straight into what I do for work. But it did, on a run, with no headphones.

What I actually think about on a run

I’ve been trying to get outside once a week this summer, Saturday afternoons, a (slow) run. Chicago in the summer is just too good to waste and I live by the water. I almost always have music on when I work out, usually at the gym. But this time my airpods were out of battery and I didn’t have time to wait for them to charge. The run was during nap time (IYKYK). This was the third time I ran (clearly a professional here), and it turns out my brain does something different when the music isn’t blasting.

This time my mind kept landing on company loyalty, of all things. Super interesting, I know. A friend brought it up the week before and clearly it stuck without me realizing. Think about our parents’ generation. You picked a company, you were loyal to it, and it was loyal back. You stayed twenty, thirty years and it took care of you. That deal has been quietly coming apart for a while now. Not many people we know stick around long (unless it’s law, consulting). And the faster AI changes which skills matter and how the work actually gets done, the less of that loyalty is left, both for us the employees, and the employers.

So here’s the question I ran the rest of the way home with. If the company and/or career path isn’t the thing you build your life around anymore, then what is?

Company and career loyalty isn't coming back. So what are you actually building on?

Something is making me a little worried

Here’s what really gets to me. I think about people a bit more senior, especially in tech, who are out there bouncing between roles, chasing the next big senior title or the exit to their name. And I wonder what happens to them if the ground keeps moving this fast. The exit doesn’t come. The title stays stagnant.

I’ll be honest, I feel a little compromised even thinking about it, because I’ve sat in that exact spot. Maybe the real move now is to learn how to own something yourself. Something small, even. To get uncomfortable, to have to sell, to hear no (I got a few no’s this week and it was HUMBLING to say the least). I am not saying this because I think it’s safer. It’s more that the old system, the one where you stayed loyal and it caught you when you fell, isn’t there to catch anyone anymore.

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We automated our bodies. Now we’re automating our minds.

A generation ago, we automated our bodies. The cars, the desk jobs, the washing machine. Our muscles got soft, so at some point we invented the gym and started moving on purpose. Nobody’s grandfather ever said “I think I’ll go work out.” They just naturally moved. Kind of like those centenarians living in Greece, or Italy, always on the move. Now everybody “has to work out.” Me included. 5x a week.

We’re doing the exact same thing to our minds right now. We used to use our intelligence to build technology. Now we feed these models everything we’ve ever written and they hand the intelligence back to us. The smartest-person-in-the-room thing we all chased? That’s the part getting cheap. Sam Altman literally talks about buying intelligence “on a meter, like electricity.” That’s wild.

We automated our bodies. Now we’re automating our minds.

So if the gym was our answer for our bodies, what’s the gym for our minds? Hold that thought. I come back to it.

The three months I wish I’d had AI for

When I went into tech, I owned the number. That was the biggest shift of my whole career, going from running the analysis for other people to being the one actually on the hook for the result. And I missed, more than once.

But owning a number comes with a mountain of analytical and busy work. I once spent three months trying to figure out which market we should go into. THREE. The TAM, the analysis, pulling numbers, half of which turned out to be wrong. Today, I could do that in a couple of days, at most. My team used to fight with HubSpot just to get their deals recorded right. Now, with voice notes and dictation and automatic follow-ups, it’s almost nothing.

I think about this all the time. If I’d had even two years ago what I have now, how much faster I could have moved, how much more I could have sold, and how much I could have helped my own team level up instead of drowning in spreadsheets and too many systems to count.

That shift is important. Because AI is eating the busy work part and it leaves the meaningful (and interesting) work for us.

The two skills I’d bet on

Here are the two that are really going to matter, no matter what this turns into:

• Judgment

• Taste

You have to know what actually matters. AI will give you a hundred options, and some of them are just completely bogus. I can’t even tell you how many times AI told me to do one thing and then the next chat told me to do the complete opposite. It’s on you to figure out which one is right, and that is not a skill that’s going anywhere. AI can do the analysis in minutes. It still can’t tell you which answer is right.

So what’s the gym for your mind?

Remember that question I parked? Here’s where I’ve landed.

I played Mahjong for the first time recently. I figured the whole appeal was the mental workout, all the pattern-matching. It’s not, or it’s not only that. It’s four people at a table, phones face down, actually together for two hours (well, only that long because they had to teach me). Searches for Mahjong clubs are up something like 4,000 percent in the last year. There’s a reason.

That’s the gym. Not just for your brain, for the human part. The real conversation with the awkward pauses. The game with no screen on the table. The people who actually know you, or are getting to know you.

And it matters more now because of this. There’s a tool out right now that builds a full talking video of you, your face, your voice, your hands, from fifteen seconds of footage. Thirty million people already use it. Most of the Fortune 100 too. Someone could be me on camera by the time you finish this email. It can fake almost anything now. The one thing it can’t make up is time.

It can copy my face in fifteen seconds. It can’t copy fifteen years of experience.

My friend who figured it out

I keep coming back to a friend of mine. Really sharp, took a new job a few months ago. Four months ago she wasn’t into AI at all. Now the thing she’s most excited about is that she finally gets to do the meaningful part of her job. The real conversations with candidates, the actual judgment calls. And she lets Claude do all the analysis that used to take her weeks to do - in just minutes now.

And it’s not just her. PwC’s 2026 jobs report found the roles built on human judgment are growing about twice as fast, with pay climbing faster too. The deciding is the part that will pay the bills going forward.

The fifteen-minute thing I’d actually do this week

Want to see this for yourself? Try this.

Open ChatGPT or Claude (if you know me, you know Claude is my go-to). Don’t sit there typing. Open a voice note and just brain dump everything you did this week, the good and the bad, out loud. Then ask it to sort it all into two columns:

1. The stuff a machine can do quickly and cheaply

2. The stuff that needs your judgment and taste, the things only you can do

Then ask it the real question. How can I use AI to do more of column one, so I can spend more of my time on column two?

Here’s what mine looked like:

1. Column one: I had Claude build out a whole go-to-market sourcing model. Who my leads are, how and when to reach out, managing the database in Notion, even drafting some of the outreach. I also built an AI Chief of Staff to feed me a prioritized list each morning based on my calendar, emails and voice dump from the night before.

2. Column two: the stuff that’s actually mine. Building out the systems for my clients, and a lot more live conversations and outreach, the kind where taste is the whole thing.

When I saw it laid out like that, column two was full of the parts of my work I actually love.

Where it’s all colliding for me

Okay, back to that RV daydream I opened with. Here’s why it won’t leave me alone.

Work changed with remote. Education might be changing too. Company loyalty is gone. AI is eating the busy work. And I keep wondering, is there actually a world now where we get to live a little more fluidly? The RV. The summer where the kids are at camp in Italy during my work hours and we actually get to be there. The honeymoon winery, except this time with our kids in the back seat.

(actual winery circa 2017 that may be our inspiration for a future Italian summer?)

As everything else gets cheaper and faster and easier to fake, the things that take real time are the ones about to be worth the most. The long (and sometimes boring) marriage. The friendships (some stay, some leave, some come back). The trip you keep saying you'll take. We keep thinking the flex is more, the bigger house, the nicer car. I'm starting to think the flex is wanting less of that, and a lot more of this. Real, in person experience.

The flex isn’t more stuff. It’s wanting less of that, and a lot more real experiences.

So this week, a couple of things. Do that two-column voice note, it’s the fastest way I know to stop feeling vaguely doomed and start seeing your own work clearly. Then take it home. Have your partner do it too, and compare. And ask the bigger one, the question I keep asking at my own kitchen table. In a world where almost everything can be faked or sped up or bought on a meter, what’s worth protecting because it takes time? Then actually put one of those things on the calendar. Not someday. This week.

And if you feel that same itch I do, the slightly worried one, sit with this too. What would it look like to own something of your own, even something tiny, before the ground shifts again?

You’re already paying attention, which honestly is most of the job.

I’ll see you after carpool.

Danielle

First, I did the homework

There is a lot of doomsday talk about AI right now, and most of us are just letting it wash over us. I didn’t want to do that. I run Numeriq Advisors, an AI team for companies, so this is basically my world, and even I needed to sit down and actually understand what people mean when they say this could end badly.

So I watched a whole documentary about it, over two afternoons, because I could not get through it in one sitting. It’s called The AI Doc: Or How I Became an Apocaloptimist. The guy making it is about to become a dad, so he sits down with people on both sides of this and asks them one simple question. Are we going to be okay. One side pulls toward we’re building something miraculous. The other says we’re building something we won’t be able to control, the kind of thing that eventually makes the world combust. He never tells you who’s right. He just lets them talk. And about halfway through, sitting in my tiny makeshift closet office (IYKYK), very much not in the dark, I realized I was more than a little scared about the world my kids are going to grow up in.

We’ve been here before

I kept thinking about Y2K. A lot of us millennials remember watching that countdown, half expecting the planes to fall out of the sky and the power grids to go dark the second the clock hit midnight. Apparently about a 20% of Americans stocked up on food and water just in case. Then it hit midnight, and the lights stayed on. We’d worked ourselves up for months over a disaster that never came.

Here’s what I’ve learned from living through a few of these (Y2K, pandemics). You spend the whole time braced for the worst, and then you mostly just have to wait and see how it really plays out.

Except this time the thing we can’t predict isn’t sitting in some lab, it’s already in our houses, in our kids’ hands, changing how we work and where our careers are headed almost every day.

Which is exactly why I’m handing this to you instead of keeping it to myself. This isn’t abstract tech news you can scroll past, it touches your job and the world our kids are walking into. So no clever prompt this week. Just both sides, because I think both are warranted, and some of what I found genuinely surprised me, starting with who turns out to be the most afraid. Let me give you the scary one first.

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How this could go really wrong

It kept me up a couple of nights, honestly. A lot of the people who are the most scared are the ones who built this technology. Not people yelling on the internet, the actual engineers and researchers who made the technology. There was even a letter that went around a few months ago, written by an AI founder, basically a warning to the rest of his world that the pace has crossed a line and most people have not noticed yet. It went viral, close to 100 million views across platforms. I sat down and read the whole thing in one sitting, and it was the first time this whole AI thing made me go, uh oh. (It’s worth a read.)

The people most scared of AI? They’re the ones who built it.

The fear, in plain terms, is that once a machine gets smarter than we are, we might not be able to steer it anymore. And because this stuff lives on everyone’s phone now instead of locked away somewhere, there are a lot more hands on it, including people who want to do real harm, which is where all the bioweapon worries come from.

And it is not just talk. A few weeks ago the government actually forced Anthropic, one of the biggest AI companies, to pull its most powerful model, Fable, completely offline, the first time that has ever happened. Fable was actually the safer version, the one that came after another model they were nervous to even release, because they worried there were holes in it and the wrong people might get their hands on it. Here’s where I’ll be honest with you though. I used Fable for about 24 hours before they pulled it, and it was awesome, and I’m a little disappointed it’s gone.

How this could go really right

Now here is the other side of the table, because it’s just as loud, and it’s the part that’s making me sleep a little better at night. They are already using AI to design brand new medicines. Peter Attia, the doctor a lot of us listen to, the one who wrote Outlive, a book I really enjoyed even if half of it was probably over my head, keeps talking about real hope for Parkinson’s in the next ten years. As someone who grew up with a grandfather who passed from it, that one makes me a little hopeful. He says the same about cancer.

Listening to him, I keep thinking, maybe our kids grow up in a world where the diseases that scare us now are just things you treat and move on from. Think about how getting polio was once this enormous, terrifying deal, and now we barely think about polio at all because of the vaccine. We might even get spoiled by it, the same way none of us think twice about antibiotics for strep or the MMR shot. Honestly, I think I might be more excited about all of this than our kids will ever be.

Here is where I have landed

So which side is right. After sitting with both, I landed right where the movie does. I’ve lived through enough of these to know the truth usually sits somewhere in the messy middle. The people sure it’s the end, and the people promising paradise, almost always both miss it.

What I’d take from it

So what do you actually do with all of that. Three things.

1. Go watch the documentary.

The AI Doc. Understand both sides, watch it for the hour and a half. It’s worth it.

2. Real talk about your career.

We’re already seeing this shift, right. Our parents and grandparents had this loyalty to one company for life, and we already see people moving around way more than that. But I think it’s bigger than just switching jobs more often. The actual way we work might change. You’ve heard me bring up Sinead Bovell before, the futurist. She talks about the end of the career ladder, a world where a lot more of us offer up our skills and work project to project instead of clocking in for one employer.

I’m sort of living that right now. I went from corporate, to tech, to building my own thing, and somewhere in there I stopped feeling like I was climbing a ladder and started feeling more like a solopreneur. The strange part is that I’m building slower than I ever did inside a company, and a lot more on purpose. There’s no one telling me if this is the right move or the next step, so I have to be really intentional, stay focused, and not go chasing every shiny new thing. It doesn’t always look like progress in the old way. But it’s mine, and it’s deliberate, and I wouldn’t trade that back.

So if you’re a little worried about your job, you probably should be, but the move isn’t to panic. It’s the thing Sinead always comes back to. Forget your job title for a second, and get clear on the skills underneath it, the actual thing you’re good at that someone would pay you for no matter where you landed. That is what travels with you when the company, or the whole way we work, changes underneath you. You don’t have to quit anything or start a business. You just want to know what’s yours to carry.

Forget your job title. The thing you're good at is what travels with you.

3. About our kids. Yes, parts of this are scary, the bioweapon stuff is a real concern and I'm not going to pretend it isn't. But they might also grow up with more medicine and more answers than we ever had. And remember, we spent our whole lives sure that nuclear war was going to end us, and it still hasn't.

The scariest version of the story is not the usual outcome.

I closed my laptop after that second afternoon still a little scared, but mostly hopeful, which I think is the only honest place to land. The fact that you’re even reading this means you’re paying attention, and that’s most of the job.

So this week, skip the kids on this one. Bring it to your partner, or a friend, and actually ask them. How do they see AI hitting their life right now, the good and the bad. What are they actually scared of. And what are they hopeful about. Then just listen. I promise you’ll learn something.

I’ll see you after carpool.

Danielle

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Everyone keeps asking what AI is going to take from our kids. I keep asking the opposite. What if, used on purpose, it gives us back some of the things we actually miss?

I was so sure I had it figured out.

Let me tell you about the Monday I found out I’d ordered my son a cookie for lunch. Just a cookie.

A little backstory. I had forgotten to order his lunch twice, back to back, two weeks in a row. If you’ve ever gotten the text from the teacher that your kid has no lunch, you know the exact feeling. It wrecks your whole morning.

So I built a fix, and I was proud of it. I took a picture of his lunch calendar and handed it to Claude in Cowork. The deal was simple. On the orange days, the ones I’d already ordered, drop a 7am reminder in my email that says “lunch is ordered,” so I don’t pack one for nothing. The other days get no reminder, because those are the ones I still prep myself. The schedule moves around, Mondays and Thursdays one week, Tuesday and Friday the next, and the thing that used to make me crazy was lying in bed at night, not remembering if I’d ordered, dragging myself back to the app to check.

It worked. The reminder came through. I felt so smart. One more nagging little thing, handled.

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And then, a couple of Mondays ago, I got a gut feeling. Wait. Did I actually do that right? My Claude reminder had already told me lunch was ordered. I logged into the app anyway. And there it was. I’d ordered him a cookie. Only the cookie.

I caught it myself, texted his teacher, panicked, grabbed his favorite pizza and drove it over. At the end of the day she told me he’d still been upset. I lost an hour of work. And a little bit of my son’s trust. I had been so sure I had it all figured out with AI.

AI did exactly what I asked it to. The catch is, it can’t care whether I got it right. That part is still on me.

Which is really what I want to talk about today.

So I went and asked someone who actually knows.

Here’s where I’ll be honest with you. I use AI all day, for my work, my business, this newsletter. And I still felt unsure about where it belongs in my family. That is an uncomfortable place to sit.

It’s also, apparently, a very common one. A lot of women are quietly sitting this out, and the research backs it up. We’re about 22% less likely to use AI than men. I feel that hesitation in my own chest. But I don’t want to be on the wrong side of it, and I really don’t want my kids to be.

So I sat down with Sarah Dooley, the woman behind AI Empowered Mom. She spent years building AI inside big companies, and now she helps families figure out how to actually use it. Her book, AI Empowered Family, is on the way. I came in with my cookie story and a hundred questions, and she handed me the one idea that reorganized everything. (FYI she also has an awesome newsletter that I highly recommend!)

Her insight: don’t start with the tool. Start with your values.

She and her husband wrote a short family mission and named a few core values before they ever made a single rule about technology. Once those are on paper, the AI decisions stop being agonizing. If your family value is a joyful celebration, then using AI to help plan the party isn’t cheating. It’s serving the thing you already care about.

Once you get clear on what you actually value, the day-to-day AI decisions kind of make themselves.

So I tried it. Here’s what came up for us.

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So I grabbed a notebook and wrote it down.

I sat with one question: what are we really protecting in this house? The same few things kept surfacing.

Security. My kids’ faces and names don’t go into AI, and they’re not on social media. That isn’t mine to hand over.

No over-reliance. The minute a tool turns into a crutch, it’s working against us.

Transparency. My kids see how and when I use it, out loud, never behind a screen.

Growth. If it’s making us sharper, great. If it’s making us lazy, that’s my cue to pull back.

Presence. This is the big one. I’ll happily use AI to amplify the real, in-person, slightly messy parts of our life. I won’t let it quietly become one more thing we lean on too hard.

Write those down and you get a single test that does most of the parenting for you.

Does this use of AI amplify presence, or replace it? If it amplifies, I’m in. If it replaces, it’s a no.

That test gets a lot clearer when you think about the kids specifically.

When do we hand them the keys?

The honest answer is that I’m still figuring this out, and anyone who tells you they have it perfectly mapped is selling something.

But there’s one idea I keep coming back to. Sarah pointed me to a framework her friend Julie Kelleher created and trademarked, called Parent in the Loop. The analogy Julie uses is teaching a kid to ride a bike. First your hands are on the handlebars. Then a hand on the seat. Then you’re running alongside, lungs burning. Then, only when it’s safe, you let go. AI is the same. With my littles, my hands are still firmly on the handlebars, and I am in no rush.

A couple of hard lines I’ve drawn in the sand. Companions are the first one. The thought of my kid pouring their heart out to an AI friend genuinely scares me, so that’s off the table until they’re much older, sixteen, maybe eighteen. I think about it exactly the way I think about social media age limits. Same logic. Same reasons.

The skills that make someone good with AI come first, long before the tool shows up. Critical thinking. Judgment. You only build those by doing things the slow, real way.

Something a friend told me has stuck with me. Her daughter, about ten, and her friends had to write a goodbye message to someone who mattered. The first instinct, instantly, was “let’s ask ChatGPT.” And I get it, I do. But that is not how a child learns to say goodbye. We want them to fumble for their own words first, to feel the lump in their throat, so that years from now, when they do have these tools, the muscle is already there. Kids reach for AI for the same reason we do. To take the friction out. But with some things, the friction is the entire point.

We do the real thing first, so the muscle is built before the tool ever shows up. AI can help them polish it later. After the thinking, never instead of it.

And once you see it that way, there’s one use of AI I’ve completely fallen for.

My favorite way to use AI all summer.

This is where the tool and the childhood I actually want for my kids finally meet.

Point the AI at the offline adventure. Then close the laptop and go live it.

Ask it for twenty ideas for a boredom jar. Have it design a backyard scavenger hunt, plan the campout, draw a pirate treasure map. Two minutes of prompting, and then it’s chalk and dirt and melting popsicles from there. The AI did the prep. We do the living.

And this is the gentlest possible way to bring a kid to the handlebars. You’re driving, they’re watching over your shoulder, and the whole payoff is something they make with their hands, off the screen completely. AI as the setup for presence. Never the substitute for it.

So here’s where I’d start this week.

Try this: the old-school list.

My actual summer list. Not a Pinterest board. The real, slightly dorky, sit-on-the-floor stuff I keep getting nostalgic for.

1. The old-school click camera. The film one I brought to camp and took on a trip. No screen to check. You just wait for the photos.

2. A Walkman. Yes, really.

3. Pick-up sticks. In my Amazon cart right now, pure nostalgia for the games we used to play.

4. Bike rides by the water. Even after camp and school. The weather is finally right for it.

5. Ice cream at the end of the day. Even when it’s already evening. Especially then.

6. Hopscotch. Chalk, a sidewalk, done.

7. A pogo stick. I got my daughter one, and it has been a hit.

8. The beach, once a month. No excuses. That one is mine.

9. Mini golf by the lake. The one my kids love.

10. Pizza down the street. Pick it up, walk it home, eat it together.

✦ THIS WEEK: THREE SMALL MOVES

1. Pick three from your own version of that list, the ones that would actually define your summer. Mine starts with the beach, once a month.

2. Write one family AI rule together, even with little kids. Ours is heading toward: “AI helps us make things and learn things, with a grown-up. It is never our friend, and never our secret.” A rule they help write is a rule they keep.

3. Use AI for just one of those three, to plan it, with your kid right there beside you. Let them watch you drive.

What I’m really after, under all of this, is simple. To stay close to the people in my house while the world speeds up around us.

So forget the perfect system. I clearly don’t have one. Get clear on what you’re protecting, and protect it on purpose.

Here’s what the cookie taught me. The lunches I botch fade fast. What sticks for my son is that I showed up, flustered, holding his favorite pizza, paying attention. Right there beside him, hands on the handlebars.

So go buy the pick-up sticks. Get the evening ice cream. Be gloriously, deliberately present. You’re more ready for this than you think.

I’ll see you after carpool.

Danielle

I came back to Montreal for a family wedding this weekend. It had been a while, and people were curious about what I’ve been up to. The newsletter, the AI consulting business, the acquisition work, the podcast appearances. Some people lit up. Some were genuinely confused. And a few said some version of the same thing: “this is so not you.”

And they’re right. The version of me they knew at 22 wouldn’t have done any of this. She was serious. She wore fancy work clothes and tried to look like she knew what she was doing. She followed the ladder because the ladder made sense, and it was the only roadmap she knew.

I used the time waiting at my gate to write in my journal. The ladder was a legitimate path for so long. It got me somewhere real. It just isn’t the best way anymore.

What I was actually building this whole time.

Let me tell you what was actually on my resume beyond the resume.

Auditor (ew). M&A consultant. Top 5 MBA grad. Tech VP.

That’s the title track. But the actual work was something different. Learning how to become the go-to person for international clients because I had built the exposure and the interpersonal range to handle it. Navigating boardrooms in cities where I didn’t always speak the language. Being one of the only women in a room of bankers and consultants for years on end and figuring out how to own the space anyway. Moving between Toronto and Montreal and overseas, multiple times. Having deals fall apart at the worst possible moment and learning how to read a room when everything had just gone sideways.

Every bit of that came with me. And it isn’t obvious from the titles.

Someone I know well got an offer at big law in New York. He speaks four languages and also has a degree from the Kennedy school (Harvard). You can say it started with a great undergrad and great early opportunities, but from my perspective he’s been stacking a kind of compounding judgment that will make him exceptional at everything that comes next.

What I mean by this is your skills outlast your tasks. It’s up to you to understand what you’ve actually built with them.

This is why its so important right now to understand how those skills compound.

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Am I (and it) really that different?

Over the wedding weekend, I learned from a good few people that they were genuinely scared about AI and what it means for their jobs. And I kept thinking: is it really that different than technology shifts before?

Think about what has happened across the last 100 years. Physical labor became cognitive work. Cognitive work became knowledge work. Now knowledge work is becoming something that requires directing and interpreting AI rather than executing the task itself. Each time, the people who adapted were the ones who could articulate what they actually brought to the table beyond whatever the current tool was.

When I was an M&A analyst, I thought the job was building financial models. What I actually got good at was going from 30,000 feet to understand a whole business and then back into the details to catch the risk that wasn’t obvious, the thing that could change the deal price or be the reason you tell a client to walk away. Building the model was the task on the job description, but the judgment was the skill that I carry to this day.

I remember being one of 7 people in a room talking about entrepreneurship through acquisition during my MBA. I was the only woman. Again. Those sessions now draw 65 or more people, and the room looks completely different. That shift is happening because more people started asking what else might be possible for them. That curiosity was always there. Now there are tools to actually do something about it (like the magic of Substack with Claude Cowork for this newsletter).

The people I’m watching thrive right now are the ones who figured out what they actually built, pointed it somewhere new, and started moving.

(There is a real risk we atrophy when we outsource too much of our thinking to AI. I touched on this last week re our kids, but it applies to us too. That conversation is critical enough to deserve its own newsletter soon.)

I know this is true because I’m living it.

I’m not the same person I was.

Here’s what I really want to unpack, because I think it’s very relevant to the shifts we’re going to be seeing over the next 2 to 3 years.

I started posting on social media and writing publicly. Which sounds small. But building in public changed who shows up in my life. I’m having conversations with people I haven’t spoken to in years. I’m going on podcasts. I’m getting featured in other newsletters. I’m getting experiences I wouldn’t have gotten if I had stayed on the typical path, which for me was: do good work, hope it gets noticed, climb the “title” ladder and leave it at that.

What I didn’t expect: posting things out loud brings people back into your world.

At 22, I was serious, more cynical (still am?), very focused on external markers. Good grades. Good company. Good title.

What I notice now is how much of that has flipped.

I want less external validation and a lot more internal. Not “did I get the promotion” but “is this mine, does this feel like the version of myself I want to be in two years?” And I’m not alone in this. I’m seeing more and more people in my circle getting genuinely curious. They are semi-panicking about AI but at the same time curious about what they can actually build and do with it.

I am not the same person I was when I left Montreal 15 years ago. I’m good with that.

So here’s the toolkit.

(FYI image above is me learning how to build a website with Claude Cowork + Lovable).

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Here’s where I’d actually start.

Two steps and one prompt.

Step 1: Run this prompt. Paste it into Claude or ChatGPT. The AI will ask you two questions — one about your professional work, one about what you do at home or on your own time. Answer by voice note or just type it out. You’ll get back a clear picture of the skills you’ve built that you’ve probably never noticed or were able to name.

Here’s the prompt:

“I want to understand what skills I’ve actually built across my life. Ask me one question about my professional work and one question about what I do outside of work — at home, in my free time, or as a volunteer. Based on my answers, give me a picture of the underlying skills I’ve developed and how they could translate into a new career direction, a passion project, or something I could start to monetize. Be specific. Don’t give me generic advice.”

From what comes back, find the one thing that makes you feel something. The one where you think: “actually, yes.”

Step 2 (Level Up): Build a Claude Project around it. A Claude Project is a dedicated workspace inside Claude that holds your files, notes, and context, and remembers it all every time you come back. A regular chat forgets the moment you close the window. A Project builds over time.

Start by pasting your skills analysis in as the foundation. Then add things as they come up: notes you kept on your phone, job descriptions that catch your eye, ideas from conversations. Claude connects the dots. It becomes a working system for figuring out where you’re going, not just a one-time conversation about it.

I’ll do a full walkthrough on how to set this up. If you want to get started before that, reach out to me directly.

And if you’re someone who feels like you’ve been on the sidelines of all of this, this last part is especially for you.

For anyone who felt like they had to sit out.

There are a lot of parents, and a lot of moms especially, who paused or shifted careers in ways that don’t map neatly onto a resume. The skills built during that time, managing complex logistics, negotiating with irrational humans, keeping a whole household running, never showed up in a title.

For a long time there wasn’t a clear way to translate any of that into what the world was calling career growth. Now there is a whole toolkit that can help you do the translation. You don’t have to be technical. You don’t have to have kept up. You just have to be honest about what skills you’ve built, and be willing to start.

The career path doesn’t have to be vertical to matter.

You have more than you think. Start there.

I’ll see you after carpool.

Danielle

A toddler on his father’s shoulders in a hotel lobby. There was an iPad propped behind the father’s head. The child was watching it. The dad probably didn’t think he was doing anything wrong. He was just carrying his kid through a lobby.

A friend described this to me. She was in Mexico on a family trip, and everywhere she looked, kids at dinner tables, kids at the pool, kids in the lobby, all watching screens. I told her I had a moment like that too, at an all-inclusive the year before. A gorgeous outdoor restaurant, a three-year-old with a tablet propped at her place setting. It never crossed my mind to do that with mine. But it’s just normal now, and most of us have barely noticed.

And then I took my daughter to the library this weekend.

There was a boy at one of the computers, maybe ten or eleven. He wasn’t watching a tutorial or doing anything for school. He was just a kid on a screen, watching another kid do something vaguely weird in a fake hospital bed. Then Minecraft. My daughter walked up behind him and stood there completely still. She said, “I want to watch that.” I said, “No, we don’t come to the library to watch TV.” She came with me.

But on the walk over to the farmers market after, I couldn’t stop thinking about it. I brought her there to get books, to be somewhere that felt like the 90s for an hour. A screen almost won in thirty seconds. It’s not that she’s addicted to screens. It’s simply that the pull was that strong. She’s four.

Screen problems are, in some ways, the old problem. The new one is harder to see. And I keep wondering: can we actually protect childhood this time? But first, you have to see what’s already happening.

We were never built for this.

I work in AI tools all day, every day. Which is exactly why something Jonathan Haidt said in a recent TED talk has been on my mind so much lately.

Haidt is the social psychologist behind The Anxious Generation, and one thing he said just clicked for me right away: humans aren’t just social like dogs or chimpanzees. We are ULTRASOCIAL, like bees and ants. Our bonding is physical and it requires bodies. Sharing meals, moving through space together, laughing together, touch. Millions of years of evolution have wired us this way. That shared, in-person, physical experience is how the connection actually happens, how it gets built into us.

I see it every single weekend with my own kids. When we spend a day with friends, actually in the same room, the laughter is different. The body language is different. The whole energy is different. And the feeling at the end of that day, compared to the feeling when you turn off the TV and everyone just kind of drifts, there is no comparison. You can see it in them. We are just so much happier when we are with people we love in real life.

And now we are building technology designed to replicate exactly that responsiveness without any of the real wiring underneath it. AI is always available. It never gets tired. It always has time for you. It sounds like what we all wish we had more of. Except it doesn’t need anything back from us. And chatbots are now being built directly into stuffed animals and toys, marketed as a companion always in the room. A friend who never has to go home. It’s worth naming what that actually is: an attempt to give kids the feeling of connection without another human being involved. For creatures built the way we are, that is not the same thing.

Human connection is who we are. It’s not optional.

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Here’s where AI is already sneaking in without us knowing

This is where the story gets harder to watch.

A therapist recently ran a session with a man and his “female partner.” The partner was an AI companion. A real session, happening right now in real time. A human being who brought an algorithm to couples counseling.

I recently caught up with a friend who has been paying very close attention to all of this, reading everything she can on what screens and AI are doing to kids’ development specifically. She told me about a girl who came home and said she used AI to brainstorm ideas for a sleepover party. That meant deferring to an algorithm for the one thing kids have been doing for themselves forever: deciding what to do on a Saturday night at a sleepover. The wrestling, the creative back and forth of actually figuring something out together, that IS the thing that builds creative thinking and judgement. And it just didn’t happen, it was mentally offloaded to AI.

She also told me about a kid who, instead of riffing with his friends to come up with a funny class song, asked ChatGPT to write it. Then everyone sang the AI’s song. I thought back to color war. The class trip bus. We’d just make something up. We’d try things out, something would come out of it, and it was ours. Now they don’t have to do that.

She called it exactly what it is: Innocent ways of stealing the kids’ creativity.

The evidence got there before we did.

We already have data on what happens when we don’t get ahead of this.

Sweden was the first country in the world to go all-in on digitizing schools, tablets at every desk, devices in nursery classrooms. After years of declining test scores, they reversed course in 2023. The Karolinska Institute issued a finding worth paying close attention to: “Clear scientific evidence that digital tools impair rather than enhance student learning.” They went back to textbooks. They went back to handwriting.

A friend posted something on LinkedIn recently about returning to handwriting that made me stop scrolling. It was talking about the almost rite of passage of having to write a ten-page essay by hand, the physical pain of it, the crossing-out and rewriting and getting the outline right. One of the most progressive countries in the world just said we’re going back to that. My friend who I interviewed for this edition kept coming back to this same point. The importance of wrestling with a writing outline, making edits, physically putting words on paper. That process matters in ways we’re only now starting to understand.

And then there’s what we already know about social media. The generation before us gave their kids smartphones young, not because they were bad parents, but because the research wasn’t there yet and the companies moved faster than anyone understood. Now we have the data. We see the outcomes. We see the kids who grew up on those platforms and we know exactly what we would have done differently.

We watched it happen with social media. We’re not doing that again.

AI is not going away. I use it every single day for work and I genuinely believe in what it can do for adults who use it with intention. But kids aren’t developmentally ready for this. They have no baseline to question what they’re being told. They don’t understand that it might not be healthy to constantly be turning to a chatbot for answers. They don’t know what’s being taken from them, the ability to critically think, build judgement and taste.

I’ll be honest about my own experience. Some days when I’ve leaned on AI too much, I feel a little off, like I skipped a step I should have taken. And I’m an adult who knows how to catch that, who can cross-reference what I’m reading and push back on what doesn’t feel right. What happens when a kid who has no baseline to question any of this gets the same access? They can type “explain this to me like I’m three years old” and get any complex idea broken down in seconds. They can skip the part where they don’t know something yet. They can skip the part where they sit with being wrong. And that sitting, the discomfort and confusion of not knowing yet, is exactly what builds the capacity to actually think.

You are not the only one who feels this way

I thought for a while I might be overcorrecting. Being the alarmist mom.

Then a friend stopped me at the park last weekend, kids running around between us, and just said it flat out: “I’m honestly just scared.” No context needed. I knew exactly what she meant. Another friend told me at dinner the night before that she’s worried about what all of this is going to do to her kids. And another friend, one I’ve talked about before, has been quietly grappling with what it even means to sit with an idea anymore, to actually think something through from scratch without immediately handing it off.

Every single person I’ve talked to about this lately has said some version of the same thing. Scared. Not sure what to do. Trying not to be the alarmist mom while also knowing in their gut that something real is happening.

The friend I interviewed for this edition has been doing the actual slow work of building norms in her community. Not petitions. Parent having conversations. Small, livable agreements people can actually hold. What I learned from her is that if you go too “all in”, you can turn people off completely. You have to meet people where they are. She’s right. And she said finding even a few other parents asking the same questions changed everything.

More parents than you think are already scared and haven’t said it out loud yet. And that’s exactly what I felt when I spoke with her. I finally felt like I’m not crazy, and there are people actually doing something about this that I can learn from. I hope we do the same thing in our community.

If this resonated, share it with a parent who needs to hear this. More parents than you think are feeling this exact thing.

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What I’m actually doing about it

Not a complete system. Just where I’m starting.

First: I’m noticing. One place in our day where AI or a screen fills a gap that used to require someone to figure something out. The boredom gap. The “I don’t know what to do” moment. I’m not fixing everything at once. I’m just seeing it. That first move matters more than you’d think.

Second: I’m finding my people. One other parent who’s asking the same questions. Not a committee. One conversation. If you’re reading this, you already know someone who would want to read it too.

Third: I picked up The Anxious Generation. If any of what you’ve read here resonated, start there. It’s not a doom spiral. It’s a diagnosis, and more importantly a case that the tide is already turning. Parents and teachers and entire countries are pushing back, and it is working.

One more thing: I’m putting together a separate email specifically about how to talk to your kids’ school about AI. There are real questions worth asking, and you’re more powerful asking them with one other parent than alone. That’s coming soon, and it’s more practical than it sounds.

Here’s what I want to leave you with: this is already working. In schools where phones have been removed, teachers report the same thing over and over, they hear laughter in the hallways again. Real laughter, between actual kids. Haidt says parents are mobilizing faster than he expected. Countries are reversing course. Parents are finding each other, setting norms, having the hard conversations. The movement is real and it is growing.

AI is coming for a lot of things. It should not come for childhood without a fight. Not because technology is bad. Because the brain being built during those years is irreplaceable, and we know too much now to hand it over without being clear-eyed about what we’re doing.

Can we protect childhood? Yes. But only if we stop waiting for someone else to start.

This week’s dinner-table question: “Is there something you’ve asked your phone or a computer to answer that you think you could have figured out yourself? Was it easier that way, or did something get lost?”

Ask it to your kids. Ask it to yourself too.

I’ll see you after carpool.

Danielle

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What we had instead was six kids between the ages of 7 and 2.5, one house, a foosball table, and each other. The bonfire never happened. The boats never left the dock. What was supposed to be boating on a lake turned into a drive to a strip mall in the middle of nowhere, Pennsylvania, where my kids ran inside and were absolutely thrilled to just have something to do.

By 7pm, I stopped checking on them. They’d figured out the foosball. They’d invented something on the curling table. They’d set up some version of corn hole I’m not sure anyone else has ever played. And all six of them were just chasing each other around the house, screaming, laughing, in a game that had no rules I could understand and apparently needed none.

I sat on the couch watching them and thought: we did not plan this. And this is the best thing that happened all trip.

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Four days, two cities, one plan that kept falling apart

This trip did not look how I thought it would, and that started before we even got to the Poconos.

We flew from Chicago to New York City on Thursday morning, spent the afternoon and evening there with family, and it was already cold. Friday we had lunch in the city, got in the car around noon, and drove up to the Poconos. It was supposed to take under two hours. It took three and a half. We stopped at a Walmart for groceries in the rain and arrived after everyone should have been in bed. My youngest refused to sleep in the pack and play, which he is probably too old for anyway, and none of us slept well.

Saturday it rained all day. Sunday morning we woke up early, got back in the car, and drove back to New York City to spend the day with family before flying home Monday morning. That’s when the nosebleed happened, mid-walk to the subway. It was pouring rain. We pivoted to a taxi, rerouted the whole afternoon on the fly, and still made it to the Lego store. By the time we got there we were too done for FAO Schwarz, which had been the plan right next door. My son fell asleep in the cab home. I was running logistics in my head the entire time while everyone else seemed fine, and honestly, I was not fine.

That is the actual trip. Four days, two cities, a round trip between Chicago and New York with a side trip to Pennsylvania, one freezing lake we never used, and a plan that kept falling apart.

And yet.

The skills my kids were building

On the drive home, I made a list in my head. Every moment that went sideways: the boating and bonfire that never happened, the indoor play space detour at a strip mall in Pennsylvania, the wrong terminal, the subway that turned into a taxi in the rain. Those were the moments doing the most work. Because of all the chaos and sideways plans.

AI is a very good assistant. It is a terrible teacher of judgment. Travel is a very good teacher of judgment. One does the planning. The other does the teaching. We need both.

Every parenting newsletter I’ve read in the last two years has some version of the same list: adaptability, critical thinking, creative problem-solving. I have never known what to do with any of it. How do you put “adaptability” on a calendar? Where does it go, between school pickup and weekend soccer?

Here is where it goes. It goes in the moment when six kids are stuck inside a house in the rain and nobody has a plan. Adaptability looked like a foosball bracket that ran until 7pm. Critical thinking looked like reading the room when your nose starts bleeding mid-walk to the subway, knowing you’re not getting underground in a rainstorm, pivoting to a taxi, and making the whole thing a different kind of New York City moment. Creative problem-solving looked like kids who ran out of things to do and invented something new anyway.

There’s research out of Harvard on how resilience actually gets built, and it’s simpler than it sounds. Not by protecting kids from hard moments. By being there with them while they work through one. Mild challenge, a parent in the next room, repeated. That’s it. I got back from this trip and realized: those were exactly the skills I’d been worrying about. I just didn’t recognize them while they were being built.

What I actually used AI for

I used AI to plan a lot of this trip. The predictable parts.

I used it to build the packing list, which took about ten minutes and covered things I would have forgotten. I used it to figure out which hotel to stay at in New York. I used it to think through whether to use our points on this flight and it helped me see that we should save them for a trip we have planned in February instead. And at the airport, I used it to find a faster path through security by going through a different terminal, where the walk to our gate turned out to be shorter than expected.

These are the predictable things. Friction removed. Not interesting.

What AI cannot do is tell you what to do when your kid’s nose starts bleeding on a sidewalk in a rainstorm with a subway entrance two blocks away. It cannot help your 7-year-old read that room and make a call in real time. It cannot make six kids figure out how to entertain themselves in a house in the Poconos when everything they planned for isn’t happening. The unpredictable things, the ones that went completely sideways, those are the ones building exactly what they need.

I’m using AI to make the trips happen. The trips are doing the rest.

Here are two prompts worth saving before your next trip (even a day trip counts!). Use the first before you leave. Use the second when you’re there.

Before you go:

“Plan a [weekend trip / day trip] with kids aged [ages]. Include ONE planned thing that might not go as expected: a backup option if something is closed, a meal that’s a stretch for them, or a 45-minute unstructured block with no plan. I want 2-3 moments of mild uncertainty we navigate together. Don’t make it hard. Make it real.”

When you’re there:

“I want to help my [age]-year-old develop better judgment in real situations. Give me 5 small travel moments — at the airport, in a new city, at a restaurant — where I can pause and let them make the call instead of making it for them. Include what to say when their call is wrong so it becomes a learning moment instead of a frustration.”

The chaotic trip was the right trip

For context: this past March we did spring break in Florida. Rented a condo, easy flight, same place for ten days, close to the beach, full kitchen. Predictable. Calm. No pivots. I probably had more fun, if I’m being honest. It was just easier.

But this trip? Four days, two cities, one freezing lake we never touched, a nosebleed in the rain, three and a half hours in the car with a Walmart stop. Pure chaos. More things went wrong than went right.

And my kids were fine. More than fine. They were adaptable in a way that I, running on less sleep with too much in my head, was honestly not. They adjusted faster than I did. I was the one on this trip who needed to learn something from them.

If your Memorial Day weekend looked like controlled chaos, compare it to your easiest trip. The easy one was probably more fun. But I don’t think it built what this one built.

This week’s dinner-table question:

Ask it tonight. Listen to the answer. They already know how to think about it.

I’ll see you after carpool.

Danielle

I did not look at my phone Saturday morning.

My older kids were already up when I found them hanging out on the couch. We made breakfast together, and then I did something I almost talked myself out of: I pulled out a week old newspaper since this weeks edition never arrived for some reason.

I’d been about to throw it out, but the Apple and Intel deal in the edition was one I hadn’t heard about and was still relevant. The piece about how China’s relationship with the West is changing was still worth knowing. So I sat down at the kitchen table and read it while my kids ate.

Nothing urgent. Nothing demanding a reaction. Just things worth knowing, at whatever pace I chose to read them.

I only looked at my phone an hour and fifteen minutes after I woke up.

And I was more myself by the time I did.

It sounds small. It wasn’t. There’s something I’ve been testing this week: no phone for the first hour after I wake up, no phone for the hour before I go to bed. And at night, before I close my eyes, I write down three gains from the day and three priorities for tomorrow. Not a to-do list. An anchor. A way to stay connected to why I’m actually doing this.

For the first time in longer than I can remember, I’m not dreading Monday. More on that in a minute.

What the elders actually say

Years ago I read a book called 30 Lessons for Living. It’s built on hundreds of interviews with the oldest Americans, people in their eighties, nineties, and beyond, asking what they wish they’d known, what they’d do differently, what actually mattered.

I’ve been thinking a lot about those lessons lately. Something is finally clicking that I couldn’t see before.

The answer was almost never a credential. Almost never a title. Almost always, it came back to two things: how they spent their time, and whether they let themselves do the thing that lit them up, or kept waiting for the right moment to start.

They wanted less. And they cared far more about where their time actually went.

For a long time, I thought this was a little fluffy. Not realistic. “Do what you love” sounds great until you’re trying to build an actual life, pay for things, take care of people who depend on you. Passion doesn’t automatically pay. I knew that.

I’ve been rethinking that though, lately. With AI, the gap between what you’re genuinely good at and what you can actually monetize just got a lot smaller. The things that used to feel like hobbies, things that couldn’t pay the bills or buy back your time, they’re becoming real options now. Not because AI is magic. Because it removes the overhead that was always the barrier between the thing you loved and the income you needed.

A friend of mine recently asked, in a joking sort of way, how can she make money on social media through her passion for cooking. What once felt like a dream can now be reality.

The elders had the wisdom. Now we might actually have the tools.

What I actually built last week

About those Mondays. A few months ago, the consulting work finally clicked into place. And this newsletter became the thing I actually wanted to build alongside it, a way to take what I’m learning and bring it to the people in my world. The two started feeding each other instead of competing for the same hours. Sunday nights feel different. And Mondays feel different too. Not something to get through. Something I’m actually looking forward to. For the first time ever.

I want to get specific here, because this whole conversation needs to stop being theoretical at some point.

Last week I built two websites. For work. Start to finish.

No design agency. No design firm. No waiting weeks for someone to interpret what was in my head and come back with three options I sort of liked.

I used Claude Cowork with Claude Design to develop the visual direction, giving it examples of brands I loved and describing in plain language what I wanted the sites to feel like. Then I built the actual sites in Lovable, which is an app where you describe what you want and it builds it in real time. I said things like:

“I want dropdown buttons here.” “Make this section bolder.” “I want this layout vertical, not horizontal.”

That was the whole thing. Me, describing what I wanted, watching it appear.

From first idea to a live site: fifteen to twenty minutes. Twice.

The skill that made the sites good wasn’t technical. It was taste. Context. Knowing what I wanted the site to communicate and who it was for. Claude and Lovable were the executors. I was the creative director. The thing I brought that no tool could replace was my own judgment about what was right.

That is exactly what the economy is rewarding right now. And if you want to know where your specific skills fit in that economy, you don’t have to wait for someone to tell you. You can find out yourself.

The quiet career scan

Three people reached out to me this week. One asking how to start making money from the thing she does for free. One wanting someone to walk her through AI for work, the way a friend would over coffee. A third with a message I’ve been getting in variations for months: “I know I should be paying attention to this, but I don’t know where to start.”

All three of them are asking the same question: is there a version of the thing I’ve been wanting to do that this actually makes possible now?

Most of us don’t realize this is available to us. We don’t have to be actively job searching to understand our market. We can scan it quietly, stay informed, know our options, without committing to a single thing.

Bloomberg published a CEO survey this week. More than 40% of CEOs are cutting junior roles and moving toward senior workers. The reason: AI handles the entry-level output now. What it doesn’t handle is the call you make correctly because you’ve made it wrong before and learned. The relationship that opened a door no algorithm knew about.

Your title is one data point. What you can actually DO is the asset, and right now that asset is more portable than it has ever been.

Run this in ChatGPT today:

“I’m a [your role] in [your industry]. Without actively job searching, what would a quiet market scan look like for someone in my position? What industries value my skills outside my current one? What kinds of roles are growing that use what I’m already good at? Give me 3 specific moves I could make in the next 30 days just to understand my options, not to change anything.”

You’re not looking. You’re informed. There’s a real difference.

Level-up: Set this up as a standing weekly brief:

“Act as my career intelligence agent. Each week, give me a 5-bullet brief: one trend in my industry I should know, one adjacent field gaining traction for people with my skills, one role type in demand I’d be qualified for, and one thing happening in my field right now I should be aware of. My field is [X], my level is [Y], my key skills are [Z].”

I have a friend who works in HR consulting. I ran this prompt to test out what opportunities could look like for someone in that world. What I got back surprised me, in a really good way.

I’m also working on a dedicated version of this for you, a tool that runs this scan automatically twice a week so the job opportunities come to you without any searching. More on that very soon.

All of this, the websites, the career scan, the Monday mornings I actually look forward to, it’s only possible if you’re telling yourself the right story about what AI actually is. And right now, most people aren’t.

The story we’ve been told about AI is wrong. Sort Of.

I’ve been watching graduation speeches this week. Students booing every time someone mentions AI on stage. I completely understand it. Something is arriving that nobody asked permission for, and that’s unsettling.

But I saw a clip where someone said something that’s been with me since.

“It’s not going to replace you. It’s just going to change how human strengths are used.”

That is the whole thing.

The story most people are telling about AI is about what it takes away. There is truth to this, but its only part of the story.

I built two websites last week using my own taste and plain language. The agency model I used to need is gone. The design firm I used to have to hire is gone. What’s left is the question of what you actually want to build, and whether you’re willing to try.

For the first time in most of our lifetimes, the friction of starting something has dropped to almost nothing. You don’t need a studio. You don’t need to finish a course first. You don’t need three free hours on a Saturday that never actually come. You need thirty minutes and the smallest possible version of the thing you’ve been telling yourself you’ll start when the timing is better.

The timing is not going to get better. You already know this.

Run this:

“I’ve been telling myself I want to [your thing] but I never start because [your reason, no time, not sure it’s worth it, don’t know where to begin]. Design the absolute minimum version I could try this week. Under 30 minutes. No setup. No commitment. Just the thing that would tell me if this is real or just a fantasy.”

Then do exactly that thing. Nothing more.

I tested this prompt out by naming my desire to help more parents use AI. A lot of the feedback I received tracked with what I am currently testing out.

One last thing

The elders in that book aren’t warning us. They’re not lecturing. They’re just telling us, clearly and without decoration, what they wish they’d understood sooner.

They didn’t wish they had waited for better timing. They didn’t wish they’d been more careful about the thing that lit them up. They didn’t wish they made more money.

They wished they had started.

You still can.

One question for tonight at the table: what's the one thing your 90-year-old self will wish you had started this week?

Ask the kids first, if they are older. Sometimes the thing they name out loud is the thing you’ve been quietly carrying yourself.

I’ll see you after carpool. Danielle

Danielle

Last week I wrote that the skills rising fastest aren’t technical. This week I want to name what they actually are.

They’re analog.

My 6 year old came running off the soccer field on Saturday with a fistful of dandelions and one sunflower he had picked up somewhere on the way. We started walking toward the car. Then he stopped, looked up at me, and asked: can I just stay and pick more?

Of course, I told him. And then I felt this little drop in my stomach, because he had to ask. The most natural thing in the world for a 6 year old on a sunny Saturday next to a soccer field, picking flowers in a patch of grass, and he had to check first to see if it was allowed.

I looked up and saw the younger two also running around, picking up dandelions and blowing them in the wind. We stayed another twenty minutes, then walked over to the park I had promised them a few weeks back, when it was too cold and rainy to go.

The next day, the library. We walked out with twelve paperbacks between the three kids and a kids’ magazine my 6 year old picked for himself. The whole afternoon felt like 1994.

They didn’t need a lecture to do any of this. They needed an hour of unscheduled time and a parent who wasn’t on her phone.

Modeling presence, it turns out, is the part our kids actually absorb. Not the lecture about screens. The version of us they watch with our hands in dirt and a book in our lap.

I kept thinking about that all week. Then a Gary Vee essay landed in my feed and gave me a frame for what I was feeling.

The middle is dying

Gary Vaynerchuk published an essay in March called “The Retail Barbell Effect.” I came across it this week. One line in particular keeps coming back:

The middle is dying.

He’s writing about brands. He could have been writing about us. The whole pitch is that culture is splitting into two extremes. Extremely digital on one end. Extremely analog on the other. The middle is collapsing.

We have all been living in that middle. The middle of mom life is the phone in our hand at dinner. The middle is half-watching the kid show while half-answering Slack while half-thinking about whether we defrosted the chicken. The middle is the AI-generated email we did not really read. The middle is scrolling instead of resting.

The middle is the part that’s killing us.

Not AI. Not the phone. Not the TV. The middle.

The real talk: I keep seeing the same content on repeat

I’ll be honest. I came back to social media a few weeks ago to amplify what I am doing here, and I am floored by how much of it is the same thing on a loop. Everyone is copying everyone. The same trends, the same audio, the same setups. The “hallelujah something hallelujah” reel format is everywhere right now. I am one more scroll away from losing it.

I cannot tell what is original anymore. AI-generated content piles on top of the copying, dressed up so we can’t tell it apart.

That is when the gross feeling shows up. Not annoyed. Not skeptical. A knot in the stomach. The “oh, this is gross to look at” feeling that you cannot really shake.

The voice in the back of my head got loud. The one that says: I refuse to lose myself to this.

I refuse to be the version of me who scrolls through the family dinner.

I have a clear mental image of the parent I do not want to become. She is half-present at everything. She does not have time to walk over to the park. She is exhausted from a life she is technically running.

That is the identity pain in its 2026 shape. We are reading the room before everyone else does.

What I tried this weekend

So I leaned hard in both directions this weekend.

On the analog end, the moments stacked up. The farmers market on Sunday morning, where one of the kids taught the others a chasing game called “stranded boat.” A basil plant we brought home and put by the window so we can watch it find the sun, basil burrata pizza already on the menu one night next week. The Wall Street Journal on the kitchen counter, with my son climbing up next to me to look at the pictures in an article about watches. A rocket ship fort taking over the living room by the afternoon. My youngest at the park, eating a piece of dirt, spitting it out, looking at me, and trying it again. He’s the third kid. If you know, you know.

On the AI end: two new things.

The first one. I had messed up my son’s lunch order two weeks in a row through the school portal. So I screenshotted the prepaid order calendar, told Claude which days were orange (already ordered) and which were red (not), and asked it to drop a 5-minute reminder on my primary calendar at 7am for the days I had paid for. The whole setup took two minutes. Now I just glance at my phone, see the reminder, and know. I will never miss another lunch order.

The second one is the habit I am picking up right now, and here is the moment that made me start. I almost double-booked our Sunday morning next week. I had made brunch plans a month ago with a friend who is hard to find time with, and meanwhile my husband had been trying to coordinate something with friends of his for the same Sunday morning. Neither of us had put any of it on the shared calendar. I caught it by accident. That was when I realized: if we don’t make this easier, we are either going to stop committing to weekend plans at all, or we are going to overcommit and let people down. Neither is what I want.

So I stopped going into Google Calendar to add things. I open Claude on my phone and talk into it. “Book brunch in the morning next Sunday.” “Friends over in the afternoon, same Sunday.” Done. The friction of opening the app, picking a date, typing it in, sharing it, that friction was what was quietly stopping me from booking the analog hours in the first place. Killing the friction is what is freeing up the weekend.

Both of those AI moves bought me back time I am now spending on the analog end. That is the barbell, working in real time.

The Amazon Prime move is coming for everything

Ten years ago, none of us decided that two-day shipping should become our default. Amazon Prime just absorbed the question of where we order from. Nobody picked. The category became Prime, quietly, on every order.

Agents are about to do the same thing, except now the categories are bigger. Which take-out we order on a Wednesday. Amazon ordering toilet paper before we even know we are out, the whole household-supply category quietly running on autopilot. Which sport we sign our kid up for next year, if we don’t keep that one for ourselves. Remember the mom from a few editions back running eleven agents? She is already there, with Amazon running the orders before she even thinks about them. This is not five years away. It is now.

Gary Vee said it plainly on a podcast in March:

“I said, Alexa, order me a pizza. If you don’t say Domino’s, you’re dead. Agents will order for you if you don’t care.”

The agent picks a default if we don’t pick first. That is the whole game. And by the time we notice, the category will be theirs.

The barbell is how we get ahead of it. Hand over the routine middle on purpose. Protect the analog edges on purpose. Either we choose, or the agent chooses for us.

The B+ mom on the front page

The analog turn is showing up in places I did not expect. There was a piece in the Wall Street Journal this weekend about a mom with three kids, ages 15, 13, and 7, who is essentially a B+ mom. She is very type A at work. At home she lets her two older kids do whatever they want across LA, as long as they are home by curfew. She doesn’t pack the weekends with concerts and coding camps and resume-building competitions. She leaves dishes in the sink sometimes. Letting go was the harder thing for her, and she did it on purpose.

The piece pointed at something a lot of us have been quietly noticing for a year now. The kids who got the most planned, the most coded, the most polished resumes? Those kids are not necessarily landing the jobs the planning was supposed to lead to. The promise we were sold (over-schedule the childhood, win the future) is just not panning out.

The analog version of childhood is not a downgrade. It might actually be the upgrade. Dirt. Boredom. Picking dandelions next to a soccer field. Walking the library with no plan. Watching mom read an actual newspaper. Building a rocket ship fort in the living room.

These are starting to look less like nostalgia and more like the strategy.

Here is how I am running it this week.

Try this before Friday

I am picking my two edges this week. I am sharing mine, and giving you three to pick from on each end. The whole exercise takes ten minutes.

Pick ONE for the AI end (the middle gets smaller)

Fully delegate. Not “help me with.” Hand the whole thing over.

1. The voice-to-Claude calendar habit. Tell Claude to schedule the time blocks and events you want this week and next weekend. Skip Google Calendar entirely. One important note: only give it access to your calendar, not your email. Calendar access alone is enough to make this habit work, and I have real concerns about handing AI broader inbox access right now. This is the habit I am picking up right now. The friction of opening the calendar app was what was quietly stopping me from blocking the analog hours in the first place.

2. The summer camp packing list. Open Claude (free) or any AI tool you already have. Paste this:

“Help me build a summer camp packing list. Camp name: [insert]. Kid’s age: [insert]. Length of session: [insert]. Quirks I want you to plan for: [list anything specific, like favorite sunscreen, favorite water bottle, whether they have their own sleeping bag or need to borrow one, favorite pillow]. Give me a labeled checklist organized by category.”

Add this one if camp packing in late May is giving you anxiety.

3. The weeknight dinner rotation. Open Claude, upload a photo of your freezer and pantry, then paste this:

“Here is a photo of what we have in our freezer and pantry. Give me five family-friendly weeknight dinners using only these ingredients. Two should have a step my kid can help with. None should take more than 30 minutes.”

If you know, you know.

Pick ONE for the analog end (the edge we protect)

On the family calendar. With a start and end time. Before bed.

1. Saturday 9-11am at home, no devices, all of us. Books, breakfast, building, dirt if the weather lets you. Phones in the box. Yours included. This is mine this week. We bought a little box for the counter, that is the rule.

2. Weeknight dinner, 6-7pm, phones in the box on the counter. The box is the rule. The least disruptive of the three. A smaller starting point if Saturday morning feels like too much.

3. Sunday afternoon at the library or a park. Bring a paperback. Leave your phone in your pocket or your bag. Watch the kids watch you. The modeling-presence move.

That’s the whole exercise. Two picks. Ten minutes. Don’t overthink it.

You’re not behind. You’re normal.

If we have been feeling this pull all spring, toward more in-real-life, toward putting the phone down, toward the library and the dirt and the dandelions, here is what I want us to hear.

We are reading the room. The two ends are exactly where culture is going, and we are getting there a beat early.

The middle is the part that’s killing us. We don’t have to fix the middle. We just have to stop spending time in it.

I am picking my two edges this week. Saturday morning at home, devices in the box. The voice-to-Claude calendar habit, locked in.

The dinner-table question we are asking tonight: “What would you do all day if we had no TV or tablets in our house?” Listen and take note of what they say. This will give you ideas of what the analog hour can look like next week.

If any of this got you thinking, hit reply and tell me what your two edges are. Or share this with a friend or someone who shares a home with you. The barbell lands better when more than one of us in the house is in on it.

I’ll see you after carpool.

Danielle

I didn’t have a clear answer. And the more I thought about it, the more I realized there was a whole stack of questions underneath the first one. Is the path they’re on actually going to lead somewhere? Will the job be stable? Will it pay them enough to live? Will they even enjoy it? And the one underneath all of those: we don’t fully know what work is going to look like in 10 or 15 years. We’re preparing our kids for something none of us can see yet.

So I spent a lot of this week digging into that. Here’s what I’m sharing today: where AI is and isn’t actually helping kids learn based on what the early data shows, the non-technical skills that seem to matter most for what’s coming, and what we can realistically do at home right now while we’re all figuring this out.

The Path Is Getting Harder to Follow

The deal most of us were handed was pretty clear. Study hard, get good grades, go to college, get a good job, climb. I know someone who did everything right. Graduated from one of the best computer science programs in the country. Came out the other side with no offers. Had to go back and specialize further just to get in the door. That isn’t a rare story anymore. Entry-level engineering jobs for developers ages 22-25 are down nearly 20% from their 2022 peak. The path that felt the most locked-in three years ago is the one taking the biggest hit right now.

As I mentioned last week, when you look at what skills are actually rising fastest, most of them aren’t technical at all. Judgment, communication, the ability to work in ambiguity, cross-disciplinary thinking. We’ll come back to what to actually do with that.

What’s Actually Happening Inside Schools

Here’s where it gets murky, and I think a lot of us feel it without being able to name it. What does this mean for school, the institutions that are supposed to prepare our kids for the real world?

McPherson Middle School in Kansas asked 480 students to hand back their Chromebooks in December and went back to pen and paper. The Brookings Global Task Force on AI in Education, covering 50 countries, put out a report in January saying that under current conditions, the risks of AI use in education outweigh the benefits. Worth pausing on though: the risk they’re mostly pointing at is kids using AI to skip the thinking entirely and submit something that isn’t theirs. That is a real problem. But it’s not the whole picture of what AI in education can be.

On the other end of the spectrum is Alpha School, and they happen to be opening a new location here in Chicago. Their AI software, TimeBack, gets students into the top 1-2% nationally on standardized tests, with nearly perfect scores. They are accomplishing this with their one-on-one AI tutoring software, which knows exactly where the student is at, teaches to their pace, and fills in the gaps specific to them. The academic instruction happens in just two focused hours a day.

The teachers are still in the classroom, but more as guides than lecturers, helping kids when they’re stuck rather than trying to teach the same lesson to 25 different kids at once.

And then the rest of the day is free for life skill activities: group debates, music, sports, building things with their hands. A friend of mine who grew up in LA said she went to a school with a similar structure: learning in the morning, hands-on activities in the afternoon.

Which raises a real question: what if the flip is a good thing? Less screen time during the school day, handled more efficiently, so that our kids have more hours for the exact skills that are rising fastest. The non-technical ones, the ones that don’t require anything special.

The Skills That Actually Compound

Sinead Bovell advises governments and global companies on the future of education, and she said something that got me thinking quite a bit:

She means reading. Playing. Debating. Building. Thinking past the immediate problem to what happens in five or ten years.

I also have a friend who works in education and has her own consulting business on top of it. She talks a lot about the importance of reading a piece of literature together as a group and then actually arguing about it. Not looking up the right answer, not having AI summarize it for everyone. Disagreeing with each other, making a case, listening to someone push back, having to rethink your position. That is a skill that compounds. And it's the kind of skill no AI tutor, however well-designed, is going to build on its own.

Here’s what the early research on AI in education is starting to show: HOW kids use AI matters far more than whether they use it. When students get uninhibited access to an AI that just gives them the answer, their learning outcomes actually go down. When they get access to a well-designed AI that guides them toward the thinking without doing it for them, outcomes go up significantly. The difference is whether the cognitive work is still happening inside the kid’s head or whether it’s been outsourced.

Kids who outsource the thinking don’t just get worse results. They develop a confidence problem. They stop trusting that they can figure things out themselves. And in a world where AI is going to be a tool in most of what they do, that self-trust is going to be the variable that separates the people who use it well from the people who just follow wherever it points.

The skills that protect against that are the non-technical ones. Reading and wrestling with what they read. Asking questions that don't have a right answer. Building things that require sequencing, patience, and the tolerance for something not working the first time. Long-term thinking, cross-disciplinary curiosity. We can build all of these at home, in small pockets, without a program or a curriculum.

The same friend who asked me if our kids would be alright also brought something up in our conversation that sparked my own thought. She framed this whole AI shift as potentially as big as the industrial revolution, and pointed out that those moments tend to unlock something completely unexpected for everyday people. The industrial revolution created leisure time. The concept of after-work hours and weekends as something separate from labor didn't really exist before it.

And my first thought when she said that was: what does this shift unlock? What if our kids get to work on things they actually care about? If AI absorbs the routine and the repetitive, what's left for people might be the work they actually want to do. The problems they're genuinely curious about, the things that light them up. A world where our kids don't have the same 9-to-5 we have, because the work that's worth doing is the work only they can choose.

I’m genuinely excited for our kids when I think about it that way.

What We Can Do Right Now

Reese Witherspoon shared recently that at her book club, only 3 out of 10 women had used AI at all. She pushed them to start. Her point was simple. Waiting to feel ready is what costs time. And most of us, if we’re honest, are in the same place she was describing. You’re not behind. You’re normal.

So here’s where we have real control, organized around the skills that seem to matter most for our kids in the world of AI.

Critical thinking and debate: Sit with a book, a show, or something in the news together and actually talk about it. Not “did you like it,” ask your kids what they would have done differently, who they think was right, what the other side of the argument is. Make them defend a position. Push back on them. The muscle this builds is the one both Sinead and my educator friend named as essential: forming a point of view and holding it under pressure.

Ask a question at dinner that has no right answer. “If you could change one rule at school, what would it be and why?” Let them argue it. Don’t resolve it for them. That discomfort is the whole exercise.

I asked my 6 year old that question this week and the one thing he said was he would want school days to become free exploration all day so they could create whatever they wanted. Which leads to the next skill.

Creativity and building: Build something with their hands this weekend. Doesn’t matter what, something out of the recycling bin, a recipe they make up, a structure that’s supposed to hold weight. The point is the cycle: trying something, having it not work, figuring out what to try next.

Let them be bored. Genuinely, uncomfortably bored. The brain that figures out what to do next with nothing in its hands is the same brain that knows what to do when everything is in front of it.

My kids want to build a full-size school bus. Not sure how we’ll do that, but that’s the type of building I could get on board with.

Long-term and cross-disciplinary thinking: Ask them where they think something goes in five years. A technology, a rule at school, something happening in the world. They don’t have to be right. They just need the practice of looking past the immediate.

Ask them how what they’re learning in one class might connect to something in another. Math and history. Science and art. Cross-disciplinary thinking builds from being asked to use it.

The AI move that makes all of this lighter:

Instead of asking AI to educate our kids, use it to help design the experiences they need without using technology. Open Claude or ChatGPT and try this:

“I have a [age] year old. I want to build their critical thinking and creativity this weekend using hands-on activities, no screens, using what we already have at home. Give me three specific ideas and what skill each one is building.”

This is how we use technology to get out of the technology. I’ve been using a version of this for my daughter, building a hands-on afternoon routine around her sensory needs without spending hours researching it or paying a provider to build it for me. It removes the burden of figuring it out yourself and leaves you with something you can actually put into practice that day.

If any of this got you thinking, or if there’s a question you’d love me to dig into, send me an email. I read everything and I bring the best questions back into future editions.

I’ll see you after carpool.

Danielle

Sharp at the Strategy. Bad at the Slides.

For most of my career, in consulting and then in a senior tech role, a real chunk of my week was building, presenting, and shipping decks. Board prep. Leadership team reviews. Client deliverables. Big strategy reads where the work was the strategy, and the deck was the wrapper.

The work itself (the strategy, the recommendation, the way the pieces fit together) was where I felt sharp. Where I struggled was the layer on top of it. The deck itself. How it had to look.

I’d sit there with my mouse, getting antsy over the positioning, and still get comments back from my boss that the font was off, when the content was what mattered, the strategy we were going to implement, the sales team I was going to run.

If you know, you know.

I’m not even mad about it now, looking back. So much comes in presentation. We see that first. The spacing matters. The alignment matters. The fact that the title font on slide seven doesn’t match the title font on slide eight actually matters, because somebody is going to notice, and quietly start to wonder whether the rest of the work was rigorous either. That’s a real thing.

There’s a lot of writing right now about AI taking jobs. This isn’t going to be one of those.

Here is what I keep finding: when I make a long list of the parts of my work that drained me, that drained the smartest, most senior people I know, almost none of them are the parts where we’re actually adding value. They're the things that have to happen around the real work, to make it presentable, to make it digestible, to get it through the door. The status update. The internal coordination doc. The reformat-this-table-by-Friday email. The repetitive-task tax that doesn’t get cheaper the more senior we get. If anything it gets more expensive, because the hourly cost of the people doing it keeps going up while the work itself stays exactly the same shape.

That’s the part nobody talks about with the 5-to-9 reality. The 5-to-9 is parenting hours for most of us. We can’t add hours on the back end the way some of our peers can. So the only way the math works is if the hours we do have count more. And the way to make them count more is by handing off the layer of work that doesn’t really need our brain to something that can do it in the background, while we stay focused on the strategy.

Whatever your version is, it probably looks something like this:

1. The Friday recap email to your boss. (It keeps your manager looped in and puts your wins on the record where they actually count. The drag is that you're the one writing the same "here's what I worked on / here's what's next" template every Friday afternoon.)

2. The weekly scorecard update. (The numbers matter, and your boss needs the read at a glance. The drag is that you're the one pulling the same three reports every Monday and copying the same five numbers into the same five cells.)

3. The meeting prep one-pager. (A good one helps the meeting run sharper, and it lets your stakeholders ride along with your thinking. The drag is that you're the one writing out what's already in your head, every single time.)

That is the part AI is really good at.

We Already Have the Half That’s Hard to Teach

There are two reports out this month worth holding next to each other.

LinkedIn just published its 2026 Skills on the Rise report. AI literacy is now at the top of the technical skills list. Nobody is surprised by that. The rest of the list is the part that surprised me. Seven of the top ten fastest-rising skills aren’t technical at all. They’re conflict mitigation. Public speaking. Stakeholder management. Communication. The stuff that takes ten years to get good at and one bad meeting to undo.

A friend sent me a screenshot this week. LinkedIn was prompting her to add AI fluency to her own profile. The platform itself was telling her to put it in the qualifications section as a skill she should be claiming. She was surprised. I wasn't, because I'm seeing it everywhere now. Her work is strategic in nature, so “AI fluency” makes sense, but it wouldn’t have been a phrase anyone used a year ago. The bar moved while we were busy.

Cognizant put out its New Work New World 2026 read a few weeks ago. The headline number: AI now touches 93% of jobs. Not might. Does.

Sinead Bovell put it cleaner than I could: “Technology literacy is the new financial literacy.” I studied finance and accounting in undergrad. Financial literacy was my whole world for three years (college in Canada is 3 years - I didn’t skip ahead). Hearing AI literacy framed the same way did something to my brain. It moved the category from “specialty” to “baseline.”

Here’s the data point that bothered me the most. In the same set of reports, the data on who’s actually been using AI in their own work shows a real divide forming. Roughly one in three women have experimented with it. More than half of men have. The gap may be about who has had a quiet weekend free of someone else’s calendar to go open a chat window and play. Some of the sharpest, most capable people I know are on the wrong side of it because their Saturday was somebody else’s birthday party and their Sunday was groceries and laundry.

If that’s where you are, you’re in the largest cohort of senior professionals right now. The reason most of them haven’t experimented is calendar pressure. Birthdays, groceries, the three loads of laundry that eat a Saturday before anyone gets to open a tab.

Some of us are the senior, ambitious, time-starved half of the workforce that has been competently running our jobs and our households at the same time. We already have the seven skills out of ten that are harder to teach. The judgment. The stakeholder feel. The communication. The pattern recognition that comes from a decade of high-stakes rooms (kids bedtime routine counts here).

We already have the half that’s hard to teach. The half that’s left is one tool, used consistently.

Outside of Work Hours

So if half the win is doing less of the drain, what’s the other half?

A friend said something to me recently I haven’t been able to put down.

“I can hear the excitement in your voice when you talk about what you’re doing now. You’re working on things you really love. Things you’re thinking about even outside of work hours.”

It was the last part of what she said that resonated with me. Outside of work hours. What our brain wanders to when no one is making it think about anything is usually the thing worth pursuing.

I Built an App on a Saturday Night

I’m figuring this out alongside you, so let me show you what figuring it out looks like in practice.

This weekend, the weather turned cold in Chicago. Three kids melting down by 11 a.m. My husband and I looked at each other in the kitchen and one of us said it out loud: why does this feel so draining?

That night, before I jumped in the shower, I opened Claude on my phone. I told it: build me an interactive summer bucket list. Here’s my zip code. Here are my kids’ ages. Indoor and outdoor. Options for one kid alone, all kids together, any combination. Things within forty-five minutes of us. And don’t just give me the farmers market, give me the categories I haven’t thought of yet.

It built me an actual app. Not a list. An interactive thing, toggleable by indoor or outdoor, by which kid was going. Sixty-five activities, some we’d done before and many we hadn’t. The biggest unlock was the toggle. I could filter by weather, by which kid was going to be home, by combinations of kids. The system was doing the mental accounting I’d usually be doing in my head. My husband laughed at me, leaned over my shoulder, and said, “So what will Claudia tell us to do today?” Claudia is his name for Claude now. I didn’t start it. I’m not going to argue with it. Sixty-five things we could do is winning in my book.

Sunday morning, I pulled up the app, saw “Kids Empire,” texted a friend who knew the place, and drove the whole family there. Old-school go-carts. Money-loaded cards. No flashing lights. No phones. Claude (sorry, Claudia) had also recommended a gelato spot a few minutes away, but the kids were having too much fun, so we just got the ice cream sandwiches at the place. No one knew the difference. No one cared. Came home happy. I wasn’t on my phone scrolling for ideas because the system already had the answer.

Same kids. Same house. Saturday vs. Sunday. The difference wasn’t that we tried harder. The difference was that the “what do we do today” overhead, the part that was eating the day before it started, got handed off to something that does that work in twenty seconds.

Here's a stat from this month: parents using AI for the family stuff are getting back about four hours a week. Family Mind's tracker has the data, and No Guilt Mom landed in the same range.

What's been fun to watch is what some friends are doing with those hours. One friend is running three projects in parallel with AI's help: child education consulting, a cooking thing, editor for a children's newspaper. A year ago none of that would have fit alongside her real life, and now she's doing all three. I'm doing my own version (you're reading one of mine), and everywhere I look, people are quietly picking up passion projects that have been on the shelf for years and just trying them. The cost of testing something has fallen off a cliff.

And before we go any further, I’m not about to suggest anyone start a side hustle on top of everything they’re already running. Permission, not pressure. The thing on the shelf doesn’t have to become a business. It doesn’t have to become anything. It just gets permission to use a single afternoon to see if it still has a heartbeat. And to see if it fills your cup the way you imagined it might.

If AI can build me a custom app on a Saturday night in 3 minutes, what could it do for that thing in the back of your mind?

A Bathroom Vanity Reno That Sat for 4.5 Years

I want to give you the smaller version too, because not every unlock looks like building an app.

This week, when my husband finished his shower, he gestured at the cabinets in the master bathroom and said, “I think we should redo these. They’re ugly.”

We have lived in this house for four and a half years. The cabinets have been ugly for four and a half years. We have talked about repainting them roughly twice a year for four and a half years. Every time I have heard it, my internal answer has been the same: forget it. Because redoing the cabinets means picking the color, which means getting samples, which means finding a painter or doing it ourselves, which means a Saturday I do not have, and I am the one who has to drive all of that, because I am the one who knows what we like.

This time I did something different. I opened ChatGPT. I cleared the toothpaste off the sink. I took a picture. I typed: I like beach coastal vibes. Give me six options of what this color could look like.

A year ago I tried this same thing in ChatGPT for a different project. It was finicky. It took me thirty minutes to get one image that looked right. This time it took thirty seconds. Six clean options. Big time difference. Big mental load difference. I had assumed white. The dark navy option was not on my list. I showed it to my husband. He said, “I like the dark one.”

Four and a half years of stuck. Thirty seconds of unstuck.

This is the smallest version of the unlock. The version that says even the dumbest stuck thing in our house can move now. Not because of will. Not because we finally found the time. Because the barrier to take the first real step dropped to almost nothing.

The bathroom is happening.

I think about how many of those tiny stuck things sit in every house. The dresser redo we keep meaning to start. The pediatric dentist switch. The closet shelving. The summer camp registration we’ve been avoiding because there are nine browser tabs involved. None of them are going to define our year. But the cumulative weight of them in the back of our heads is real, and a lot of it can move now in fifteen-minute pockets we already have.

Two Things to Try This Week

One for the work half. One for the rest. Both small.

Move 1 — Name your drain. Hand one piece of it to AI.

This week, pick one piece of the drain at your job. Hand it to AI. See what comes back.

Step 1. Open one of these in a new tab:

• Open ChatGPT

• Open Claude

Step 2. Paste this prompt in. (Or hit the microphone icon and brain-dump it like you'd brain-dump it to a friend on a walk. You don't have to type it.)

I’m going to brain dump the recurring tasks at my job that drain me — work I don’t actually enjoy and isn’t even what I’m best at. (Examples for me: the weekly recap email, the scorecard report, the meeting prep doc.)

When I’m done, I want you to do three things:

1. Rank what I described from EASIEST to HARDEST to take a meaningful piece off my plate using AI today.

2. For each task, name the AI tool or capability that fits best (ChatGPT, Claude, Gemini, Notion AI, ChatGPT Projects, etc.) and one sentence on what it does well for that task.

3. Pick the EASIEST one and give me the exact next step I could take in the next 15 minutes — including a starter prompt I can run today.

Don’t give me twenty ideas. Pick the smallest, most useful next move.

Here’s my brain dump:

Step 3. Type or speak your brain dump after that prompt. Send. See what comes back.

Move 2 — Notice where your brain wanders.

This week, just notice and write down. What does your brain wander to when no one is pushing it to think about anything? Walking the dog (I don’t have one, but maybe you do). Folding laundry. The five minutes between meetings. Whatever you keep coming back to, write it down. Don’t do anything with it yet.

Next week, I want to start digging into what AI is actually doing to school, and what we want our kids walking out of it knowing. Open question I keep sitting with: what do we want them to be able to do, when school can’t move fast enough?

I’ll see you after carpool.

Danielle

It is 8:47 on a Tuesday night. There is one lunchbox still open on the counter. The toddler is in his crib, refusing to sleep, babbling at the ceiling. There is a work email I have not opened. And tomorrow is “market day” at school, where my kid is supposed to bring in “fake market items” to trade with fake money, and I still do not really understand how much fake money he is supposed to have, or what counts as a market item, or whether I missed a parent email about it three days ago.

Mental load is real.

There is a book on my mantle called Fair Play. My husband bought it, with genuinely good intentions. Eve Rodsky wrote it. The premise is simple and a little brutal. There are roughly 100 invisible “cards” that run a household. The doctor appointments. The snack restock. The birthday party RSVPs. The camp signups. The lunchbox washing. The school form signing. The running mental tally of which kid needs more socks, because the drawer is full of single ones and missing is somehow better than orphaned. In most households, those cards are not split evenly. They are sitting in one person’s hand.

I have not opened the book. I have circled it. I have walked past it. The hardest part of Fair Play, and most of the advice about mental load, is also the first step: get what is in your head out of your head, into a format somebody else can actually pick up and run with.

Which, it turns out, is something AI is unusually good at.

A Real-Life Receipt From Last Saturday

Before I get into the AI part, let me give you a real one that happened to me last week, because it captures the cost of the mental load better than anything I could write in the abstract.

My son started a new soccer league this spring. He had his first session two weeks ago. I told him that if he liked it enough to keep showing up, we would buy him cleats. The cleats had been sitting on my mental list ever since. Just the cleats. Nothing else from that morning.

This past Saturday was supposed to be his second game. I got everyone dressed, packed three kids in the car, and drove to the lakefront where the field is. We pulled up. Nobody was there.

My husband looked at me with The Look. The “are we at the right place” look. I called a friend whose kid is on the team. She said the words every parent hates to hear: “Oh no, you missed the email.” It had come in the night before, in the DREADED window, those few hours between school pickup and bedtime when nothing in your life is opened, read, or processed. The league had cancelled because of rain in the forecast. I never saw it.

We salvaged it. The lake was right there. The kids pulled scooters and bikes out of the trunk, and we spent the next hour and a half on the path along the water. It was actually one of the better mornings we have had in weeks.

But I want to be honest about what happened, because the salvage is not the point. The cost was not the missed email. The cost was the look. The friend I had to call to confirm I was the dummy. The little tape in my head all afternoon that said you should have caught that. And the small but real moment where my husband briefly questioned my logistics.

Now multiply that by 14 of those a week.

That is what we are actually talking about.

The Real Talk on AI and Mental Load

I am going to be honest with you. There is no AI tool, no app, no prompt, no magic 11-agent setup that is going to take the mental load off your plate completely. I wish I was making this up. I have looked. I have downloaded the things. There is no silver bullet.

But there are two things AI is genuinely good at right now, and both are shifting how I run our week.

1. Getting what’s in your head out of your head

This is the unlock. Here is exactly how I do it.

I open the Notes app on my iPhone. I hit the microphone. I start talking. Everything that is in my head, in whatever order it shows up. “Cleats for [son]. RSVP for the party on Sunday two weeks from now and add it to the calendar. Dentist for little one is this week, cannot remember which day. Book the NYC trip for Memorial Day weekend, check if our Chase points cover it. Did I reply to the school newspaper Q&A. Out of trash bags. [Kid] needs new socks.” I keep going until my brain is empty. No filter. No order. No punctuation.

Then I copy that whole dump, open the Claude app (if you do not have it yet, just download Claude from the App Store and use the free version, it takes 30 seconds), and I paste it in with this prompt:

“Make this into a list I can hand off to someone else. Group it by category. Prioritize by level of importance.”

That is it. That is the prompt.

What comes back is a clean, organized, actually-shareable list. Sorted by bucket (kids, household, logistics, calendar) and ranked so I know what is actually urgent versus what is just loud in my head.

The part nobody talks about is when I actually do this. I do not sit down for it. I never have. I do it on a walk. I do it while the kids are playing in the living room by themselves (which, as you’ll see in a minute, is something I am doing on purpose). I do it while I am making dinner with my phone propped on the counter. I do it in the two-minute window before I walk into school for pickup (there isn’t a line, that is just where I have my best ideas). Whenever the spill shows up, I just catch it.

Then I hand the output to my husband and say “Tell me which ones you’ve got.” FYI he’s doing the annual check ups this week. The list itself does not reduce the load. It makes the load handoff-able. And once it is handoff-able, it is actually splittable. That was the whole breakthrough for me. I was not carrying it alone because it was mine to carry. I was carrying it alone because it was stuck in a format no one else could pick up.

2. Doing the boring middle steps

The other place AI is really earning its keep is in the soul-crushing logistics. Two real ones from this week.

The school newspaper Q&A. My kids’ school newspaper sent me a Q&A to fill out. Questions about our family, our values, how my kids spend their time. I was actually excited about this one. The school does this for a good reason and I wanted to share our story. I just kept running out of time. So yesterday I finally opened Claude, hit the microphone, and babbled the answers in. Ten minutes later, I had clean, thoughtful responses I felt good about. The thing I had been meaning to do for weeks got done while I was eating a salad.

The Memorial Day weekend NYC trip. We had been saying for four months now that we would go to NYC to meet friends. I kept opening Google Flights, getting paralyzed by the options, and pushing the decision out another week. Last week I finally pasted everything into Claude: “Here is where we are going. Here is what we are prioritizing. Choose the airline and best flights for our preferences. Map out hotels in this area. Figure out if it is worth us using our Chase points, and if so how.” I had been carrying every one of those considerations in my head, trying to make them all fit at once. Claude laid them out in a table. We finally booked it that night.

Two things that had been hanging over me for weeks, both crossed off in under twenty minutes. None of this is hard. All of it is relentless. Stack 14 of these a week and you have half a workday back.

A Quick Side Note on the Eleven Agents

A friend sent me a podcast this week about a parent who, fully unprompted, built 11 AI agents to help run her homeschool. Eleven. One for math, one for reading, one for logistics. I listened to the whole thing on one drive. It was wild. It is also not me. I do not have 11 agents. I have a voice memo habit and one really good prompt. If you are hearing about people doing wild things with AI right now and feeling behind, please remember that I, the person writing the AI newsletter, do not have 11 agents either. You’re not behind. You’re normal. Start with one prompt. Build from there.

A Quick Detour to Business School

Quick detour. In 2018, I was in grad school, and some friends and I had an idea we submitted to the New Venture Challenge: you take a photo of the inside of your fridge, cross-reference it with your family’s preferences and dietary needs, and get a meal plan plus a grocery list for the gaps. We did not even get in. We were cut at the application round.

That feature now lives in approximately every consumer AI app on earth and costs nothing.

The lesson is not that we saw the future. We did not. It is that you do not recognize the tool you actually need until you become the person who needs it. A lot of us are right there with AI right now, looking at the noise, not sure if it is for us. It is for you. Specifically you. The version of you who is holding 100 invisible cards at once.

The Prize Is Not the Output. It’s the Time.

Here is the reframe I keep coming back to.

When I save 20 minutes drafting a piece for my kid’s school newsletter, the 20 minutes is the prize. Not the answered Q&A. The answers were always going to get sent. The question is whether I sent it during a window where I was also supposed to be making lunch, or whether I sent it in a matter of minutes and used the time back to go outside on a walk. (Newsflash: I did exactly that, right after I sent the Q&A back.)

That is the actual upside of AI for parents right now. Forget the grindy LinkedIn-influencer version of productivity. The real win is that AI buys back the parts of the day that get eaten by admin, so we can put them somewhere else. A walk. A book. A workout. A real conversation with a friend. Five quiet minutes with a coffee. Whatever the thing is that fell off the list when the kids showed up.

And sometimes, the place to put that time is back into our kids in a way that has nothing to do with productivity at all.

On Boredom, Paint, and a Cardboard Bus

Last week we talked about getting kids outside, in the dirt, off screens. This week I want to take that one step further, inside the house.

Earlier this week, my oldest pulled out every container of paint we own, lined up three cardboard boxes from our recycling pile, and announced he was building a bus. The two littles decided this meant they were also painting, but with less of a plan, and by the time I looked up, they were painting the cardboard, the floor, and each other’s arms. My husband walked in, looked at the chaos, looked at me, and said something to the effect of, “you know you do not have to let them do this.”

I know. I am letting them do it on purpose.

The more I read, the more I am convinced that the single most important muscle I can build in my kids in the AI era is being okay when nothing is happening. The ability to be bored. The ability to make something out of nothing. The ability to get into trouble in their own imagination and figure out the way back out. None of that gets built when I am hovering, narrating, and presenting them with the next perfectly curated activity.

A caveat, because I know. My kids are old enough to be feral in short bursts. If yours are still in the safety-pin-in-outlet years, this is not a “leave them alone for an hour” play. Start smaller. Dump a cup of dry rice into a mixing bowl with a measuring spoon, put it on a kitchen towel, and walk 15 feet away for 10 minutes. A wooden spoon and a Tupperware lid is a drum. Two couch cushions and a blanket is a fort. The game is not “disappear.” The game is “stop narrating their play for ten minutes and see what they do.” That is the muscle. It scales up as they do.

And the quiet side benefit: when they are playing by themselves, that is when I open the Notes app, hit the microphone, and dump everything that is in my head. The unlock on both sides of the house is happening at the same time.

Try This Before Friday

Pick the version that matches where you are this week. One is a low-stakes win you can run solo in two minutes. The other is bigger and worth it if you are ready. Both work. Neither requires a subscription or a setup (just a simple App download).

Option A — The Easy Win

(Start here if you haven’t prompted much yet.)

The School PDF Date Extractor. Dig up that PDF your kid’s school sent for next month, the one with the field trip and the half days and the 10th professional development day of the year. Open Claude (free in the App Store) or any AI tool on your phone. Upload, screenshot or paste the PDF. Then paste this:

“Here is a PDF from my kid’s school. Pull every important date, deadline, event, half day, and required item out of it. Format it as a list I can drop into my calendar. Flag anything that requires a parent action with a star. Sort by date.”

Give it 10 seconds. You will get back a clean list you can copy straight into your calendar. No emotional labor. No difficult conversations. Just five to fifteen minutes of your life back, and the quiet confidence of knowing you did not miss the pajama day.

Option B — The Bigger Swing

(Use when you’re ready.)

The Mental Load Dump. Open the Notes app on your phone. Hit the microphone. Say, out loud, every single thing you are currently tracking. Don’t filter. Don’t organize. Just talk until you run out. Copy what you said, paste it into Claude, and add this:

“Make this into a list I can hand off to someone else. Group it by category (kids, household, finances, social, medical, school). For each task, label it as a one-time, weekly, or recurring item. Rank it by level of importance. Format it so I can text it to someone or print it for the fridge.”

Send the result to your partner, a friend, grandparent or whoever else is in the thick of it with you. This one is less about the list and more about finally having the conversation with something to point at.

I’ll see you after carpool.

Danielle