WHEN THE WORLD IS BEING REBUILT

24. The School I Wouldn't Send You To

"They are born, then put in a box; they go home to live in a box; they study by ticking boxes; they go to what is called 'work' in a box, where they sit in their cubicle box; they drive to the grocery store in a box to buy food in a box; they go to the gym in a box to sit in a box; they talk about thinking 'outside the box'; and when they die they are put in a box. All boxes, Euclidian, geometrically smooth boxes." —Nassim Nicholas Taleb

Kiddos, I owe you a hard letter about something I once treated as sacred.

I grew up in an Asian family rooted in Confucian values, which is a polite way of saying I grew up believing that school was a holy thing. You sat down, you worked hard, you got the grade, and at the end of the corridor there was a Good Life waiting for you. I played that game well. I jumped through every hoop they put in front of me. And then I spent my twenties watching the real world and slowly realized that almost none of it had prepared me for it.

I'm writing this letter because I don't want you to inherit that quiet lie unexamined. Not because I think school is the enemy. But because if I don't say this clearly, you'll absorb the same assumption I did — that this particular institution, in this particular form, is the only way to become a person worth being. It isn't.

Let me tell you about the week that made this go from a vague suspicion to a thing I am willing to argue out loud.

Five days in Hong Kong

A while ago I spent a week in Hong Kong teaching kids — ages roughly ten to seventeen — about AI and entrepreneurship. Most of them had never written a line of code. Many of them couldn't have told you what AI actually was when they walked in. By day five they had built real, functioning web apps. One team, led by a ten-year-old, built a sign language transcription tool. A few years ago that would have been an impressive college senior project. She built it in a week.

What struck me wasn't just what they built. It was their faces. Several of them told me, almost shyly, that this was the first time learning had felt like fun. The first time they'd been allowed to be creative without a rubric watching them. The first time they hadn't been bored. You could feel it in the room — they weren't memorizing definitions for a test. They were making something. They were learning fast because they were learning toward something they cared about.

Meanwhile, back at their actual schools, these same kids were forbidden to even touch AI. The tools that will define the rest of their working lives — banned from the classroom. Taught by adults who, for the most part, don't understand them. And we tell each other this is the proper way to learn.

I drove back to my hotel that night and the question wouldn't leave: if a week can do this, what on earth are the other twelve years doing?

The factory underneath it all

The honest answer is that the system you and I both passed through wasn't designed for what we want it to do. It was designed in the nineteenth century to produce reliable industrial workers. The ringing bells were factory whistles. The rows of desks were assembly lines. The standardized tests were quality control. The whole architecture — the uniforms, the silent obedience, the raised hand to use the bathroom — was about producing a particular kind of person: someone who could sit still, take instruction, and perform a repeatable task on schedule.

It worked. That's the unsettling part. It still works. It still produces, very efficiently, exactly that kind of person.

The problem is that the economy it was designed to staff has been disappearing for fifty years and will be substantially gone before you're old enough to remember any of it. We are training children for jobs that won't exist, with methods that punish exactly the traits — curiosity, contrarianism, risk-taking — that the next economy will pay the most for.

You'll hear this argument and your first instinct will be the same one I had: "Surely it can't be that bad. People have been going to school forever." Let me try to convince you otherwise, gently, by walking through the parts I think are most broken.

One size fits no one

When a system has to teach thirty kids in a room with one adult, it teaches to the middle. The faster kids get bored. The slower kids get lost. Everybody loses a little.

This isn't because anyone is malicious. It's because the system is optimizing for the wrong thing. National curricula are designed to be measurable, gradable, and defensible to a school board — not to maximize any individual child's potential. What's easy to grade is a multiple-choice test. What's easy to manage is uniform pacing. So that's what you get. The whole machine is administratively convenient and educationally mediocre.

The result, repeated across millions of classrooms, is a generation taught that the goal of learning is to hit the rubric. Not to make something. Not to find what you love. To hit the rubric. By the time most kids leave school, they've learned, deep in their bones, that learning is something done to them, on someone else's schedule, for someone else's grade.

I want you to know that this is not what learning is. Learning, when it's working, is the most fun thing a human being gets to do.

I keep a copy of Mitchel Resnick's Lifelong Kindergarten on my desk because it gives this intuition language. Resnick runs the MIT lab behind Scratch, the programming environment millions of kids learn to code on, and the whole book is an argument that the best learning in human life happens in kindergarten — kids messing around with blocks and paint and other kids — and that we then systematically beat that mode of learning out of them for the next twelve years. His phrase is the "four P's": projects, passion, peers, play. That is exactly what I saw in the Hong Kong room. A ten-year-old picks a problem she cares about, plays with the tools, asks her friends for help, ships a working thing. The same kid spends Monday morning back in a regular classroom learning to ignore the part of her brain that lights up. The tragedy isn't that schools are bad at teaching content. It's that they're effective at teaching kids to suppress the very mode of learning that would make them formidable adults.

The international school version of the same trap

You might be thinking: "Okay, that's regular school. What about the fancy ones?" In many ways, those are worse. They've become luxury branding. In Hong Kong, families spend the equivalent of millions of dollars on "debentures" — not for tuition, just for a shot at a preschool interview. I have friends whose one-and-a-half-year-old children have done ten interviews. Toddlers, in interviews. For a Michelin chef's lunch program.

Behind the gleaming campuses and the swimming pools, a lot of the actual teaching is being done by expats on career breaks — well-intentioned generalists who have never built the thing they're teaching. If you wanted to learn investing, would you go to someone who's read about it, or to someone who's actually built a portfolio? In any other domain we'd answer immediately. We accept a much lower bar for the people teaching our children.

I'm not saying every teacher is bad. The best teachers I had genuinely changed me, and I'm grateful. I'm saying that the system around them makes it almost impossible to do the work they got into the field to do. They get measured on test scores. So they teach to the test. And when a kid lights up about something — actually lights up, the way I saw those kids in Hong Kong light up — the teacher has to say, gently, "We don't have time for that."

That sentence, said often enough, kills something.

What I actually believe about learning

So if I think the system is mostly broken, what would I want for you instead? Let me try to answer that in plain terms, without pretending I have it all figured out.

I believe the basics — reading, math, writing, the foundations — can be taught much better by AI than by a classroom of thirty. There's a school called Alpha School where kids learn 2.6 times faster than their peers, in two hours a day, using AI-assisted tools. Not because the AI is magic, but because it adapts to the individual. It slows down where they're stuck. It speeds up where they're flying. They get to work at the edge of their own ability rather than the median of the class. That's where mastery actually happens.

I believe the things that matter most — leadership, communication, persuasion, judgment, courage, taste — can't be taught from a textbook at all. They have to be lived. Warren Buffett didn't learn investing from a lecture. He shadowed Ben Graham. You want to learn to run a restaurant? Run one. You want to learn marketing? Try, badly, to sell something. The intangibles only land through doing.

I believe the best teachers for that kind of learning aren't credentialed by the state. They're practitioners. People who have actually done the thing. A parent who's built a business. A neighbor who's an artist. A retired founder. A coder who shipped something real. Passion and lived experience matter more than a teaching certificate, by a wide margin.

I believe school should look more like a workshop and less like a waiting room. Build. Present. Share. Reflect. Repeat. If you spent twelve years on that loop instead of twelve years on multiple-choice tests, you'd come out a completely different kind of person.

And I believe — this is the one I'm most certain about — that the most important skill you can possibly develop is the ability to teach yourself anything. The world will keep changing. The tools will keep changing. The credential I might have earned at your age is going to be worth less and less. The one capability that compounds across every door you'll ever walk through is the one where you can say: "I don't know this yet. I'll figure it out."

That is, in the end, what I want for you. Not a degree. Not a school name. The ability to learn anything.

The thing nobody says out loud

Here is the harder truth, the one that makes me uncomfortable to write. For a lot of families, school is mostly babysitting. Parents are exhausted. They're working too hard. They hand twelve formative years of their child's life to an institution that has barely changed in a hundred years, not because they believe in it, but because there's no obvious alternative and everyone else is doing it.

If you ran your business this way you would go bankrupt. If you hired your most important team this way you would fire whoever did the hiring. But because it's school, and school is what everyone does, we accept a level of slow, impersonal, unaccountable performance that we would tolerate from no other institution in our lives.

I'm not saying this to make you feel guilty about going to school, if you go. I'm saying it because I want you to know what the thing actually is, so you can choose your relationship to it with clear eyes.

What I think I'll actually do

I keep getting asked, half-jokingly, whether I'd send my own kids to a traditional school. The honest answer is: probably not in the way most people mean it. Not because I want you to be weird or sheltered or strange. Because I want you to be ready for the world that's actually coming, not the one your parents grew up in.

The world that's coming will reward curiosity, agency, judgment, creativity, the ability to use AI as leverage, the ability to teach yourself, and the ability to make something real. It will punish, with increasing harshness, the things school selects for: obedience, rote performance, hitting the rubric, sitting still.

So what I'd love to build for you — and I mean genuinely build, not just talk about — is something more like a workshop. A small, dynamic, high-agency learning experiment. Real practitioners as guides. Real projects. Real audiences. The basics taught by AI on a personalized schedule, the intangibles taught by doing, all of it grounded in the actual texture of life rather than the abstraction of a classroom.

And I'd love it to be portable. Not locked to a zip code or a school district. Imagine a world where, whether you're in Bali or Lisbon or Nairobi, you could drop into a local learning hub — same guides, same projects, same peers, just a different timezone. Learning following the rhythm of real life, not the other way around.

These are still early ideas. I might be wrong about parts of them. I'm sure I'll change my mind on details as I actually do it. But the core of it I'm pretty sure about: that learning, done right, is faster and deeper and more joyful than the system has led us to believe — and that the version of education I want for you looks much more like the energy I saw in that room in Hong Kong than like the school I went to.

The honest counterargument

Let me give the other side its due. The case for traditional school is real. It gives kids social practice. It gives them exposure to people they wouldn't otherwise meet. It provides structure when parents can't. It produces, for some kids, real friendships and real mentors. And it's a known quantity — you mostly know what you're getting. That matters, especially when the alternatives are unproven.

If you go through a traditional school, you won't be ruined. I went through one and I turned out, mostly, okay. The thing I would beg you to do — the thing I wish someone had told me — is to treat the school as one input among many, not as the whole of your education. Extract what's useful (the friends, the discipline, the exposure) and build the rest of your real education yourself, on the side, deliberately. Read what you actually want to read. Make the side project. Talk to the practitioner. Find the mentor who's done the thing. The school will measure you on its rubric; you should be measuring yourself against something much more honest.

What I want you to take from this

You will probably go to some kind of school. That's fine. What I want you to know, while you're inside it, is that the building is not the same thing as your education. Your education is a much bigger and more interesting project, and it's yours to direct.

Be skeptical of the rubric. Be curious past what they ask you to learn. Build things on the side. Find the adults outside school who have actually done the thing you want to do, and bother them with questions. Use AI to learn faster than your classmates — not to cheat, but to actually understand. Notice what makes your eyes light up, and follow that signal harder than you follow any grade.

And if, at some point, the school you're in is genuinely getting in the way of the person you're becoming, tell me. I'll listen. We'll figure something else out. There is more than one path through this.

I love you. I want you to be the kid who comes out of all of this thinking: "What do I want to learn next?" — and knowing exactly how to go find out.

Love,

Dad.