My son is about to turn six months old. Last week, he got his hands on one of those stacking rings. He held it, turned it over, and then, with this look of total concentration, tried to fit it onto the post. He missed. Tried again. Missed again. On the fourth attempt, he got it. Pure triumph.

I watched this tiny human run his own experiment. Trial, error, adjustment, success. No one taught him. No one gave him the answer. He figured it out.

Then I picked up my phone and saw a post from Nat Eliason announcing a new high school program through Alpha School: make $1 million by graduation, or get 100% of your tuition refunded. A school promising to produce teenage millionaires using AI.

I looked back at Roman on his play mat and thought: what does this kid actually need to know by the time he starts high school in 2040?

Entry-level job postings in the U.S. dropped 35% between January 2023 and June 2025. ServiceNow's CEO predicted that college grad unemployment could hit the mid-30s in the next couple of years. Goldman Sachs estimates up to 300 million jobs globally could be affected by generative AI. After cutting nearly half of Block's workforce, Jack Dorsey predicted that "within the next year, the majority of companies will reach the same conclusion." Block's stock jumped 24% that day.

The traditional playbook was simple: good grades, good college, good job, retire. That playbook is breaking down in real time. By the time Roman is old enough to use it, it may not exist at all. So what do we teach him instead?

Here is what my husband and I have been talking about.

In 1984, Benjamin Bloom proved that a student tutored one-on-one performs better than 98% of students in a traditional classroom. He called it the "2 sigma problem" and challenged educators to deliver that kind of personalized learning at scale. For 40 years, nobody could. AI is the first real shot at solving it.

But there is a critical distinction. A kid who asks ChatGPT for the answer to a question is simply copying homework. Research confirms it makes learning worse. A kid who uses AI as a Socratic learning partner, one that adapts to how they think, asks what they believe the first step is, and adjusts when they are stuck, is building a completely different muscle. Tools like Khanmigo, now operating in hundreds of school districts, are built on exactly this principle.

The most valuable skill in the AI era will be the ability to structure your own learning and know the difference between getting an answer and actually understanding something. It starts with stacking rings.

AI is the most capable generalist ever produced. It can write passable copy, generate serviceable analysis, and produce reasonable first drafts of almost anything. If your child competes with AI on breadth, they will lose. The value is shifting to the person who can evaluate what AI produces, spot what is wrong, and ask better questions.

IBM's CHRO said it plainly: "The entry-level jobs that you had two to three years ago, AI can do most of them. You have to rewrite every job." A diploma tells an employer your child sat in a room for four years. Critical thinking tells an employer they can be trusted with decisions. I know which one I want Roman to have.

This is where Alpha School gets interesting, even if you have questions about the model (and I do). They use AI to compress academics into two hours per day. The rest of the time, students work on real projects: food trucks, businesses, musicals. Their new entrepreneurial track promises students will generate $1 million in revenue by graduation, or get their tuition fully refunded.

Is that realistic for every student? Probably not. The results have not been independently verified, and tuition ranges from $10,000 to $75,000. But the underlying principle is sound: teach kids to create, iterate, and ship, not just to consume and memorize. A teenager today can build and launch a product using natural language. The kids who learn to take ideas from concept to reality will have a massive advantage over the kids who only learned how to pass exams.

When Pav and I got married in our early twenties, we were both in debt. He became obsessed with tracking every dollar on a spreadsheet. Watching the debt shrink became satisfying. Then watching savings grow. Then investing. That early discipline is the reason we have choices today that most people our age do not.

Most schools still do not teach personal finance. Kids graduate without understanding compound interest, tax brackets, or why their 401(k) match is free money. In a world where companies can restructure entire departments overnight and the stock price goes up, financial literacy and multiple streams of income are survival skills. We will teach Roman about money the way Pav taught himself: tangible, trackable, and real.

Empathy. Reading a room. Navigating conflict. Making someone feel heard. These are the skills that make someone a great leader, a great partner, a great parent. No model, no matter how advanced, can simulate them.

As more work gets automated, the people who rise will be the ones who can build trust, lead teams through uncertainty, and make ethical calls with incomplete information. These are the skills that got my husband hired as Chief People Officer at The Athletic. And they start early, with how you talk to your kids about their feelings, how you model empathy at the dinner table, and how you let them fail and sit with the discomfort instead of rushing to fix it.

Roman is almost six months old. He does not know what AI is. He is just trying to get that ring on the post. But as his parents, our job is to start asking the right questions now, while we still have time.

The old playbook was: good grades, good college, good job, then retire. The new one is still being written. But it looks more like: learn how to learn, build things, stay adaptable, own your financial future, and never stop developing the one skill no machine can replace.

And honestly? That sounds more free to me.

What are you doing to prepare your kids for the age of AI? Hit reply and tell me. I read every response.

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