WHEN YOU'RE OLDER

29. Birthday Musings — A Year Closer to Death

"It's good to ask yourself once in a while: if I die tomorrow, is there something that I felt like would still have been missing?"

Kiddos, I wrote this letter the night of my twenty-ninth birthday. It had been a quiet one. I'd spent the afternoon with your great-grandmother — the same afternoon I wrote you about a few letters back — and the slow weight of that visit was still sitting with me. There's something about helping someone in her nineties reach for a glass of water that makes a birthday feel less like a celebration and more like a kind of arithmetic. Another year added to my side of the ledger. Another year subtracted from hers.

I came home that evening, poured myself a glass of something I didn't really need, and sat down with my notebook. I wanted to write down whatever I'd actually learned. Not the things I was supposed to have learned. The things that, after a year of watching myself live, had survived.

What follows are some of the lines I wrote that night — distilled, cleaned up a little, but not improved. I've kept the ones I still believe and dropped the ones that read, in the morning, like the kind of thing you say to sound wise but don't actually live by.

These are notes from one twenty-nine-year-old to a few kids I haven't met yet. Use what's useful. Discard the rest.

I should say, before the list starts, where the form came from. The Marcus Aurelius copy I've written you about — Meditations, the one I've been carrying since my early twenties, the one that sits on the nightstand — is the closest thing I have to a template for what follows. The strange thing about that book is that it was never meant to be a book. It's the private notebook of a Roman emperor writing to himself, at night, in his tent, after long days he didn't always want to live through. He wasn't trying to teach anyone anything. He was trying to stay sane and stay honest with himself, one entry at a time. That's the only reason it's still useful eighteen centuries later — because the form is so unguarded. What you're reading below is, structurally, a much smaller and clumsier version of that. A twenty-nine-year-old, on his birthday, writing to himself in the only way he knows how to stay honest with the next year. The fact that you'll read it eventually is incidental. The point of writing it was to find out what I actually thought.

Nothing is durable. Achievements fade. Heartbreaks fade. Objects break. Memories distort. Relationships drift. Even the people you love most are on a clock you cannot see. The whole point of this letter is that you should treat that fact not as a tragedy but as the reason anything in your life matters at all. Savor it while it's here. Don't postpone the gratitude until you've lost the thing to be grateful for.

You will suffer for something. That's not the question. The question is what you choose to suffer for. The freedom we get isn't freedom from pain — it's the freedom to pick a pain that, on the deathbed, you'll be proud you carried. Pick carefully.

The reward is the journey, not the trophy. I used to think the destination was the point — the title, the exit, the validation. The older I get, the more I notice that the parts of my life I actually cherish are the in-between bits. The early-morning train ride. The bad first draft. The friend I made on the way to something that didn't work out. The trophy you eventually get is smaller than you imagined. The journey, in retrospect, is larger.

The toughest battles in life are against yourself. Not your boss. Not the market. Not the people who don't like you. The hardest fight is sacrificing short-term comfort for long-term growth, day after day, when nobody's watching. Discipline. Restraint. Doing the hard thing first. The version of you that's hard to defeat from outside is the version that has stopped sabotaging himself from within.

Jealousy is pointless. I have yet to meet a single person whose life I would actually want to trade for — fully, in every detail, including all the parts they don't post about. From the outside, everyone seems to be winning at something you're losing. From the inside, everyone is carrying something. Trust this. It will save you a lot of wasted wanting.

Trust your gut more than you think you should. I used to dismiss this as soft-headed advice. Then I noticed that almost every time I'd gotten something seriously wrong in my twenties, I'd ignored a quiet "no" that my body had been telling me before my brain caught up. Your subconscious has been keeping a more honest record of who you are than your conscious mind has. Listen to it more.

Avoid the risk of absolute ruin. Physical, financial, or to your independence. The healthy man wants ten thousand things. The sick man wants only one. Most upside is recoverable. Some downside is not. The discipline is to keep playing games where the worst case is "I lose this round" and not "I lose the ability to play."

Avoid the hedonic treadmill. I've eaten the twenty-five-course Michelin tasting menu. I've shat it out twenty-four hours later, like everyone else. The expensive version of any pleasure is not meaningfully better than the cheap one once you adjust for novelty. The trap is convincing yourself, slowly, that you need things you don't, until you've built a life that requires more income than you can sustain without compromising what you actually wanted.

Be unique on purpose. Stand out. Hold contrarian opinions, weakly held but seriously meant. Lean into the idiosyncrasies that make you you — they are the only thing the world cannot copy from you. The market for being a slightly-better version of someone else is saturated. The market for being the only version of you is wide open.

Compete in games you're naturally suited to. Play to your strengths. Don't waste your one life trying to become marginally better at something you'd never enjoy. Find the games where the things you love doing happen to be the things that win, and play those instead. The world is large enough that the right game exists for you. The work is finding it.

Pick friends by who they are, not what they've done. I went through a phase of picking friends by accomplishments. Then a phase of picking by proximity. Now I pick by values. I'm lucky that some of my closest people score on all three, but if I had to keep only one criterion, it would be the third. Accomplishments fade. People reveal who they actually are over decades. Choose them like you'll be choosing them for decades, because you will be.

People are people. Emotional, irrational, distracted, carrying things you don't see. The hardest skill in dealing with others — especially when something has gone wrong between you — is remembering that they are not behaving according to a logic that will be obvious to you. They are behaving according to a logic that is obvious to them. Learning to manage your own emotions when other people are at their worst is, more than any technical skill, what makes you good at relationships.

Compete only with yourself. The true measure of your life is whether you lived up to the standards you set for yourself — not the ones your parents, your peers, or your country wanted to impose on you. Outside competitors will always exist. There will always be someone richer, faster, more famous. The only competition that ends is the one with yourself, and only if you decide it does.

Amor fati. Love your fate. This one I've been saying to myself for years now and I still don't fully live by it. The basic idea: most of what happens to you isn't yours to choose. The reaction is. The ancients knew this. They were right about most things, including this. The peace is in the response, not in the event.

The Serenity Prayer. "God, grant me the serenity to accept the things I cannot change, the courage to change the things I can, and the wisdom to know the difference." I keep coming back to this one because almost all of my mistakes in my twenties were variations of confusing one of those three categories for another. Fighting battles I couldn't win. Accepting things I could have changed. Or — the most common — not knowing which was which.

Bonus: the older I get, the less I feel like I truly understand. This is the one that surprises me most. At fifteen, I was certain I had life figured out. At twenty, I was certain I had been wrong at fifteen, but had now figured it out. At twenty-five, same loop. Now, at twenty-nine, I notice that the people I most admire share one trait: a comfortable looseness about their own conclusions. The certainty drains out as the experience accumulates. I take this as a good sign rather than a bad one. The most dangerous people I've met are the certain ones.

A few that didn't quite make the cut, but I want to keep

Some of these I scribbled down and almost cut, but they kept coming back when I went on walks the next week:

That when in doubt, say yes to events, opportunities, and meeting people — the larger your platform, the larger the surface area of your luck.

That hobbies — for me, pickleball — have done more for my quality of life than almost any other choice I made in my twenties. Physical fitness, new friends across cities, regular hits of structured joy. Don't underestimate them.

That it's good to ask yourself, once in a while: if I die tomorrow, is there something I'd regret not having done? If the answer is no, every additional day is a bonus. If the answer is yes — go do it. You're on a clock.

That density and quality of time with the people you love matters more than the quantity. Especially now, when so many of my friends are starting families and the easy hangs of our early twenties have quietly disappeared.

That building is more fun than managing. I missed this when I was younger. I'd worry about scaling and structure and titles. The actual joy of work, I've come to think, is the part where you're making the thing — not the part where you're maintaining it.

That a perfect path through life doesn't exist. The messiness is what makes the story interesting. The scorecard at the end is only against yourself.

I read all of this back the next morning, in better light. Most of it still held up. A couple of lines I'd written felt sharper than I'd meant them to be, and I softened them. A couple felt softer than I'd meant, and I sharpened them. The rest I left.

What I want you to know is that this isn't a list of conclusions. It's a list of working hypotheses from a guy who is still figuring out his life, on the night he turned twenty-nine, written for kids who haven't been born yet. The version of me who writes you the same list at thirty-nine, if I'm lucky, will probably disagree with some of these. He'll be right and I'll be right. Both lists will be honest snapshots of someone trying.

If there's one thread I want you to pull out of all of this, it's the one underneath the rest: that you only get one go at this. Not in the morbid sense. In the practical sense. The years are passing. The clock is real. The people you love are on their own clocks too, and most of them are shorter than yours. Live like this is true, because it is.

Cheers to a good year ahead. And, eventually, to a good one for you.