I’ve known Ryan Holiday forever.

My first time meeting him, he was a marketer for American Apparel. Correction: THE marketer.

He was 26. And we emailed.

This was long before he was “Ryan Holiday™,” the bestselling author. Long before he owned a ranch outside Austin where he writes books that end up on everyone’s nightstand whether they know it or not.

Last week, Ryan and I sat down for a conversation on his newest book, Wisdom Takes Work: Learn. Apply. Repeat.

Instead we wandered into the territory books come from—life, fear, curiosity, purpose, the quiet machinery behind every page.

And also AI. Everyone talks about what AI can do. We talked about what it can’t.

Here’s the first thing:

A.] AI Is Great at Everything Except the One Thing That Actually Matters

I’ve been around AI for decades. I love it. I use it constantly. It can out-memorize me, out-organize me, out-write teenage-me.

But there’s one place no model can reach: wisdom.

Ryan said that “Wisdom is a verb.” And instantly I knew he was right.

AI can spit knowledge at you until you choke on it. Wisdom, though?

That’s the scar tissue. The mistakes. The humiliation. The repetition. The ways you slowly learn your own blind spots.

AI doesn’t have any blind spots. Which is the biggest blind spot of all. It never says, “I don’t know.”

Meanwhile, my kids argue with me for five minutes and suddenly I realize: “I don’t know anything. Literally nothing. Why am I arguing?”

That’s wisdom. Or at least the early symptoms of it.

B.] Wisdom Requires Doing the Painful Thing

I told Ryan something I’ve learned the stupid way: You can read every book on standup comedy, but until you're holding the mic and sweating through your shirt? You haven’t learned anything.

Ryan agreed. He told me about David McCullough—the famous historian—who didn’t just write about Truman running to the White House the night FDR died…

He went to the Capitol himself and physically retraced Truman’s exact route. Running the exact stairs. Feeling the exact burn.

You know what can’t do that? AI.

If AI had written that biography it would’ve said: “Truman ran down the hall.”

AI compresses. Humans feel.

Huge difference.

C.] Pain Is Tuition, Not Punishment

I always say this about entrepreneurship, comedy, writing, marriage, parenting—whatever:

The pain teaches you. The lack of pain teaches you nothing.

Ryan said: “Wisdom is the byproduct of doing the hard thing over and over.”

Not reading about the hard thing. Not summarizing the hard thing. Not outsourcing the hard thing. Doing it.

Wisdom is what’s left after the ego burns off.

D.] Curiosity Is the Gateway Drug

Ryan’s kid asked to listen to a podcast about the history of Disneyland. That’s not exactly his niche. But he thought: “Why not? Let's see where this leads.”

Curiosity is the seed. Wisdom is the tree.

If you follow the curiosity—even if it seems trivial—you end up somewhere unexpected. Sometimes somewhere life-changing.

Every major thing I’ve done—every book, business, skill I’ve picked up—started with some dumb question I was embarrassed to ask out loud.

Maybe that’s the foundation of wisdom: Not being embarrassed to chase stupid questions.

E.] Age Doesn't Make You Wise—Letting Go Does

Ryan said something that I think everyone over 35 should tattoo on their forearm: “There are stupid old people too.”

Age doesn’t guarantee anything. Some people go through life getting hit with the same lessons over and over and over and never learning a thing.

It’s not the years that matter. It’s the pivot moments.

Two brothers beaten by police as kids. One goes one way. One goes the other. Two business partners face a failure. One grows. One ossifies.

The pivot is where wisdom sneaks in.

Or doesn’t.

And what determines that? This was Ryan’s grenade: “You have to be willing to let go of the idea that you already know.”

That’s it. That’s the whole thing.

Wisdom is the opposite of certainty.

F.] The World Changes. The Wise Adapt.

We talked about academics who cling to their old theories like life rafts. We talked about older people who insist the next generation is “lost.”

Meanwhile, kids are playing piano better than the greatest pianists of the 20th century.

A teenager can learn chess openings it took grandmasters years to uncover. People learn languages in months that used to take lifetimes.

Not because they’re smarter, but because their environment changed.

The wise don’t fight the new rules. They explore them.

The Conversation Is the Wisdom

There’s a lot of things AI can’t replace. Wisdom is one of them. Not because it’s incapable of generating answers.

But because wisdom isn’t answers.

Wisdom is the shared moment where two humans try to figure the world out together, then walk away slightly less wrong than they were two hours earlier.

That’s all wisdom is. Slightly less wrong.

And that’s enough to build a life.

Click here to listen to the whole conversation. (It’s a good one.)