Letter to 20-Year-Old Me

Damn.

You turn 50 this month. Crazy, right? We’re not supposed to say anyone is old anymore, but damn. That’s kinda old.

What you can’t understand (but what I wish you could) is just how fast it goes. I know everyone says that. But it’s true. I was you, like, last week. Whatever else you get from this, please accept you don’t have nearly as long as you think. More than one person you know hasn’t made it this far. I promise your priorities will shift when the first of them dies.

What that means is that what I think is important is not the same as what you do. You have expectations about what your life would be like at 50. I remember them. But then you still believe procrastination is something you’ll grow out of tomorrow.

What I am is a direct result of the choices you made, and you’re about to make a doozy, one I’m still paying for. What it is doesn’t matter. Really. If I told you, you’d only focus on that and ignore the real problem, which is how you make decisions: out of fear.

Yes, you do. You’re afraid of failing. You’re afraid what people will think. I know exactly what you want to do and I know why you’re not doing it. You’re picking the safe path, the one where, if you show up and check all the boxes, a modest amount of money and status are virtually guaranteed. You’re hoping that might impress some girls.

It won’t. Girls aren’t impressed by box-checking, nor should they be. Fortunately for you, striving for anything makes failure unavoidable. You’re about to face-plant in a giant steaming pile of it. But that’s okay. That’s how we grow.

That seems backward to you, doesn’t it? Your whole life has been a parade of matriculation, of tests passed and standards met. Isn’t success how we grow? Failure seems like such a dirty word, perhaps the dirtiest. You’d rather someone call you a jerk or even a bigot than a failure. Those other things seem like they can be grown out of, but failure feels like a permanent stain, like being a felon.

It’s not true. In fact, anything genuinely worth pursuing won’t be easy to master, which means to get good at it you have to fail—typically a lot. We call this practice. The practice of life is experience.

You care so much about politics—way, way, way too much, by the way—because it seems to offer answers on loan, ahead of any experience. You don’t actually have to do anything to save the world. You don’t even have to leave the house! You just have to check the box on the right opinion—and get mad at those who don’t share it, I suppose.

If you really wanted to make the world a better place, there are any number of things you could do. You could find a child from a broken environment and commit the time and resources necessary to alter the trajectory of their life. Multiple organizations can connect you. The results will compound.

Or—keep making a spectacle of your opinions. See which has the bigger impact.

You are in charge of your life. Maybe that seems obvious, but a great many people don’t want to be. It’s a lot of work, and there’s no one to complain to if things don’t work out.

You’re not off to a great start. You put off walking as a toddler and you put off dating as a teen and now you lament not being active or attractive. It’s true your teen years didn’t matter, not in any real sense, but that’s why they were the perfect time to practice. You can screw up without screwing everything up. Making mistakes in adulthood has genuine consequences.

Over the coming years, the confident, well-adjusted women in your peer group—there are some—will start looking for a man who has his shit together. This will not be you.

Oh, there’s no cramming for this test. It’s already too late. You’ll try to rush it, but by the time you’re ready, they’ll all be married and you’ll serve a long ten years before and after a brief abusive marriage.

Honestly, that’s a tough break. I don’t envy what you’ll have to go through. Part of it is just bad luck. But part of it is a result of the choices you made. Like most young people, you don’t realize that the person in your life who will lie to you the most is yourself. It isn’t that you convince yourself of outright falsehoods. It’s that you rationalize away what you don’t want to do.

Meeting people is awkward. You’re right that you won’t find a girlfriend at a bar. That’s true. But you won’t find her on a dating app either. And the people you DO meet at bars, parties, and concerts are the friends of the women you will date, including—finally—your wife.

It’s quite a story, like something out of a novel. I won’t spoil the adventure by telling you.

You’ll want to know about money. You’ll want to know if we’re rich.

You don’t know it yet, but you don’t want to be rich. You think you do, but you don’t. You want bags of money to fall out of the sky. That’s not the same.

You’ll get close enough to wealth to see it’s achievable. You’ll experience a little of what comes with it and also what it requires, what you have to sacrifice in trade. You won’t be interested.

There’s a study published sometime between you and me in which a large sample of people over a century old were asked about life and regret. Exactly zero of them said “I regret not caring more about money” or “I really wish I would’ve spent more time at the office.” A few lamented missing out on an investment opportunity that could’ve altered the course of their life (cough cough Bitcoin cough), but that’s not the same. (That’s bags of money falling out of the sky.)

You have to make a living, but not at the expense of making a life. We will have high income and we will have no income, and we will be happy and we will be sad, and above a certain minimum, there doesn’t appear to be any relation.

Life is bumpy like that. It’s some kind of law. Everything in the universe oscillates, from light waves to planetary orbits. Your career, your beliefs, your hobbies and interests, your waistline, your engagement with friends and family, and yes, your fortune, will all undulate over time.

You’ll feel the blast of a terrorist’s bomb from just down the street. You’ll stand barefoot in the water atop an 800-foot waterfall. You’ll jump out of a perfectly good airplane and off a perfectly good bridge. You’ll never feel more alive. You’ll hold a human heart in your hands and spend hours in dissection. You’ll walk on five continents and swim in three oceans (so far). You’ll never ingest anything that gets you as high as your first full-sky view of the Milky Way. You’ll meet the love of your life on the far side of the world and drop everything to woo her. You’ll learn there is no fortune worth the things you now take for granted. You might want to work on that.

Also, dogs.

That’s it. Any wisdom I have doesn’t stretch much beyond these words.

Good luck.

P.S. Really, please, just stop with the politics already.