Your second choosing.

Some of the most important decisions of your life are made before you even know who you are as a person.

When you’re 16 or 17, you’re asked to pick what you want to study. By 21 or 22, you’re entering a field you likely know very little about. What company should you work for? What city should you move to? What should your life’s trajectory look like for the next 50 years?

You’re basically a kid. How the hell should you know?

Last week, Moses Kagan posted something on X that summed this up nicely. He said you basically enter a tunnel around 15, come shooting out around 35, and the rest of your life is largely determined by the choices you made and the luck you had inside of it.

I agreed with him immediately. But the more I read it, the more I felt irritated by the idea that it was true. Because those twenty years are nuts.

You’ll choose a career before you've worked a full year anywhere, accept a job in a city you've visited once or twice, and start chasing money because being broke sucks. You’ll go after the definition of success you inherited from your parents, and then eventually from your friends, peers, and bosses.

And why wouldn’t you? You have to choose something. Who has the luxury of sitting around until you're 40 so you can “fully understand yourself?”

By 40, you’ll have lived through thousands of workdays. You’ll know what sixty-hour weeks do to your mood, your relationships, and your health. Whether having a big house feels good or if it’s just a status symbol you have to begrudgingly maintain. How much money is enough for you and your family. And if the work that once drove you forward still feels exciting.

The frustrating part is that by the time you finally have enough information to make a better decision, you feel less allowed to make one.

I've started thinking of this moment as your second choosing.

The first choosing happens when you're young, life is coming at you fast, and you have pretty bad information. The second choosing happens after you've spent a few decades finding out who you are, what your choices led to, what they cost you, and, most importantly, whether you still want the same things as 22-year-old you.

Sure, you’re probably still guessing a little. But you're not going in blind anymore.

And yet, a lot of people never choose again. They treat the decisions they made at 22, with the least information possible, as the decisions they have to stick with forever. “Well, that’s what I do for a living.” “This is where I have to live.” “I've already spent fifteen years building this.”

Old choices begin sounding very permanent.

I think that deep down inside, so many people want to change. Who they are. What they do. Where they live. I know I did. And, if you’re anything like me, maybe you’re secretly hoping to hit a point that forces the change.

A layoff gives you permission to change careers. A health scare “wakes you up” to what’s important. A breakup gives you permission to move somewhere new and start over.

What we really want is an excuse nobody can argue with. Something that lets us say, “I had no choice.” Because saying, “I don't want this anymore,” can sound foolish, immature, silly, or ungrateful, especially when you’re in a position that other people would kill for.

But what if nothing has to go wrong?

What if you just look around and say to yourself, “I no longer choose this.”

Of course, choosing something new doesn't mean you wash your hands of everything and leave everyone else to clean up your mess. That would be silly. Maybe you’ve got a spouse, children, some debt, or people who depend on you. Those responsibilities are important, and your choices obviously affect more than just you.

But everyone has responsibilities. And responsibility isn't the same thing as needing permission. It just means you have to consider more than yourself when you choose again.

Maybe you’ll choose again and end up choosing the same life you already have. Doing the same work, living in the same city, hanging around with the same people, with the same priorities. Great. But there’s a big difference between staying because you’re afraid to question your old decisions and staying because, after everything you’ve learned, you’d make the same choices.

I think Moses is right. The years from 15 to 35 shape an enormous amount of what comes next. The decisions you make, and the dumb luck inside that tunnel, probably explain a huge part of the life you're living today.

But what would you choose if you were choosing again today?

You’ve spent years learning what you want. Maybe now you should choose accordingly.