How To Raise A Thinker In The AI Era [WRAP 208]

Hey Reader,

We’re planning year-end assessments for our oldest this week. He’s in fifth grade, we homeschool, and part of the process is figuring out where he stands compared to other kids his age.

So my wife and I did what we do—talk about it in 3 minute bursts between meals, diapers, baseball practice, laundry, and bedtime. We talked about what should a ten-year-old actually know at the end of fifth grade? And more importantly… does the answer to that question even matter the way it used to?

💡 One Big Idea: The Four Skills That Actually Matter

Here’s what I keep thinking about: a huge chunk of my grade school education was memorization. State capitals, multiplication tables, dates of battles, the order of planets. The way you learned those things was textbooks, encyclopedias, and the library. I used to read those Encarta encyclopedias on my dad’s Mac. That was the whole internet for me until high school.

Then Google showed up and you could find anything in seconds. Now you can ask Claude or ChatGPT and get a thoughtful, sourced answer faster than you could type the question into a search bar.

And honestly? I think that’s mostly great. Because how many of those facts I memorized in elementary school still matter today? Basically none.

But there’s something my wife and I keep thinking about whenever we poo-poo the memories of memorizing and all the “useless” things we learned.

The facts weren’t really the point. The point was the process of learning them. Figuring out how to find information. Sitting with something you didn’t understand and working through it anyway. Sticking with a problem when you wanted to quit. That’s what was actually being built underneath all those worksheets and flash cards—not a database of trivia, but a kid who could think.

And what I’m worried about as a dad is that my kids look at AI the way I looked at a calculator in fourth grade. Why would I do this myself when the machine does it better?

The crazy thing is that AI will solve a lot of problems. It already solves a lot of mine. I built two web apps with it a last week. But there are some really important things about being a human that no model is going to handle for you.

So as our oldest heads into middle school, my wife and I are focused on these four skills:

Thinking

Can you look at a situation, break it down, and figure out what matters? Not memorize the answer—actually reason through it.

Learning

Can you teach yourself something new when nobody’s making you? Not because it’s assigned, but because you got curious and followed the thread. This includes using all the tools the internet and AI give him!

Problem-solving

Can you get stuck and not quit? Can you try something, watch it fail, and try something different? This is the one AI is most likely to short-circuit, because it makes the stuck part feel optional.

Communicating

Can you explain what you think and why you think it? Can you write clearly, talk to adults, disagree respectfully, and ask good questions?

I believe those four are the most important skills any kid can develop right now, and they’re only going to get more valuable as AI gets better. Because the more machines can do the routine stuff, the more we need people who can do the human stuff. And I want my kids to know the difference between using a tool and letting a tool use them.

📹 Video to Watch: Wright Thompson on How I Write

Wright Thompson is one of the best nonfiction writers alive, and this interview with David Perell on the How I Write show is worth your time. Thompson talks about the craft of reporting, putting in the reps, and how writing is more about architecture than words.

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A couple things I love about Wright: he still lives in Oxford, Mississippi, when most writers at his level would’ve moved to New York or LA a long time ago. And he likes to move around town while he writes—coffee shop, then the library, then somewhere else. There’s something about that restlessness that I relate to.

If you’re someone who cares about doing good work and getting better at your craft, this one’s for you. Skip to about 51:44 for his thoughts on the brainstorming process.

Quick note: Wright cusses a good bit. Just a heads up.

📰 Article to Read: How to Be a Writer with a Day Job

Mason Currey writes a great Substack called Subtle Maneuvers about the daily routines of creative people. This piece is a personal one, Currey talks about being told at twenty-one that if he wanted to be a serious writer, he should move somewhere cheap, get an undemanding job, and write on the side.

I find this really interesting, and it might surprise some of you to hear this: even though I work for myself and run a successful business… I’ve still mostly ended up giving myself what amounts to a really great day job.

I’m a full-time newsletter coach and marketing consultant who also makes YouTube videos and writes newsletters like this one. The coaching and consulting pay the bills. The writing and creating are the things I’d do even if they didn’t.

Maybe that’s not so different from what Mason’s professor was talking about.

Thanks again for reading the WRAP, I'll talk to you again next week.

Matt Ragland