Letter to Jack
Dear Jack,
Congratulations on finishing high school, and I am glad you landed on a college you are excited about. You were always a good kid. Now you get to find out what kind of man you are going to be.
School handed you a schedule for eighteen years. The rails are about to start thinning out. By the time you reach my age, the schedule is whatever you choose to make it.
The unglamorous truth is that most of an adult life is repetition. What you do on most Tuesdays is who you become. You are at the start of choosing what to repeat. Hold onto this. Everything that follows comes back to it.
Yourself
There is a voice in your head that has been talking to you your whole life. It was there this morning when you woke up, and it will be there on your last day. You will spend more time with that voice than with anyone you will ever love. How the two of you get along will shape your life more than anything else.
You already know this relationship has good days and bad ones. The night you lie awake replaying the dumb thing you said. The morning after you did something hard, when you catch yourself standing a little taller. The hour you lose because some part of you did not want to start. That is the two of you, getting along or not.
You keep score on yourself, whether you want to or not. Every time you do the thing you told yourself you would, the voice trusts you a little more. Every time you do not, it trusts you a little less. Nobody else can see the scoreboard, and you cannot stop keeping it. How you feel about yourself is mostly that record: thousands of small promises, kept or broken.
You will break some of them. Everyone does. You cannot unmake yesterday, but you can wake up every morning and keep the next one. The voice keeps a tally, not a verdict.
Most people would rather not look at the scoreboard. What they don’t want to see is the gap between who they meant to be and what they actually did, so they look anywhere but the mirror. And the longer you look away, the harder it gets to look at all, until the relationship goes untended and you drift. Your life is still yours; it just stops feeling that way.
If you are not at home with yourself, nothing external will fix it. Not the girlfriend, not the money, not the next thing. You will get it, enjoy it for a week, and start wanting the one after it. You cannot outrun or outsource this relationship. The work is internal, and it is yours.
This sounds heavy at eighteen, and it is. The good news: the work is small and daily. Do the thing you said you would. Tell yourself the truth about how it is going. Sit alone with no screen once in a while and see who shows up. Keep your promises to the voice, and it will be good company for the rest of your life.
Who You Marry
After your relationship with yourself, nothing will shape your life more than who you choose to spend it with. Get this right and your life expands. Get it wrong and everything else shrinks with it. Take your time with this one.
A good partnership is one of the best things adult life has to offer. The best of it is quieter than the movies promise: someone who has seen all of you and is still glad when you walk in the door, the one who laughs with you at things no one else would understand. The joy of partnership is the joy of a good thing repeated day after day. A year in, it’s nice; twenty years in, it’s the ground you stand on.
And once it holds, everything else finds its proper size. You can take real swings, and you can miss, because the most important thing is already secure. You can build the things that take two people and a long horizon: a home, a family, a life with some weight to it. My own best years are the married ones, and most of the best lives I have watched up close were built the same way.
Dating is an audition. Marriage is the show. Dating asks how someone shows up when she is trying: charming, dressed up, fun on a Saturday night. Marriage gets the whole person: the good days, the dull ones, and the ones where she is tired, broke, or afraid. Anyone is wonderful on a trip to Rome. The real question is who she is on a wet Tuesday.
So watch for the show, not the audition. The way she looks will change with the decades; the way she treats people mostly will not. Notice how she is with the friend who has nothing to offer her and the gate agent who just canceled her flight. The show is full of moments like these.
Her family deserves your attention, because her people could become your people. The way her parents treat each other is the model she grew up with, and most people repeat that model whether they mean to or not. You will learn a lot at the first Thanksgiving.
Getting close to someone will also teach you about yourself. Does she make you bigger or smaller? Do you have to perform? The question is not whether you like her; that part will be obvious. It is whether you like yourself when you are with her. With the right one, the answer keeps coming back yes.
All of this runs both ways. Everything you look for in her, she should be looking for in you. You only control your side, so the work is not just finding the right person. It is also becoming someone worth wanting.
You are not picking a wife at eighteen. You are starting to notice. Meet people. Have fun. Never forget how serious this game is. And when you know, go all in.
The Attention Arcade
Imagine your attention as tokens. You wake up with a finite number every day, and by the end of the day they will be gone. The world is an arcade, and every machine in it is designed by a professional whose entire job is to take your tokens. Look at me. Care about this. Be angry. Be afraid. If you aren’t paying attention to this, you are a bad person.
The machines change every decade, but the game stays the same: the argument between strangers, today’s outrage forgotten by tomorrow, the highlight reel of someone else’s life. Love them or hate them, the token still drops. The newest machines conveniently fit in your pocket.
You can walk past the machines. You do not owe any of them a token. Every token they get is one you handed over.
A rich life comes from spending your tokens on things that matter. Build something. Learn something. Love somebody. The tokens will be gone by midnight either way. The only question is what you bought.
What you pay attention to is what you think about. What you think about is who you become. Most of who you are at thirty will be downstream of where you put your attention at twenty.
Pick Your People
You absorb the people around you the way your clothes absorb campfire smoke: not by doing anything, just by sitting close long enough. Their normal slowly becomes your normal. If they lift, you lift. If they complain, complaining starts to feel like conversation. Ambition is contagious. So is cynicism.
For your whole life until now, you have not really chosen who is around you. Your family was given. Your classmates were given. Your neighborhood was given. College is the first time you pick, and it matters more than it ever has.
Some of what you pick is the place itself. A city’s vibe is just its people at scale, and it works on you the same way. Some cities make the life you want easy; others make it nearly impossible. When the time comes, notice where the people doing the work you want to do actually live.
Every so often, look around and ask: do I want to become like these people? Notice how you feel after you spend time with someone, not just during. Some people light you up in the room and leave you drained on the drive home. Spend your time with the ones who leave you better than they found you.
You do not find your people by looking for people. You find them by doing things. Join the team, take the class, show up at the thing that interests you — whoever is already there is your kind. Then keep showing up. Friendship is mostly repetition: the same faces in the same place, week after week, until one day you realize you found them.
You are somebody else’s normal, too. Be the one who pulls them up.
Avoid Cliffs
You will make a lot of mistakes. Almost all of them can be fixed. You will recover from the bad grade and the bad job and the bad haircut, and you will laugh about most of it by thirty. So forgive yourself for those and keep moving. Carrying a mistake you already survived is just taking the same hit twice.
But a few mistakes are cliffs: one step too far, and there is no climbing back. Driving drunk. Having a child with someone you barely know. Debt you cannot pay. A habit that stops being a choice. An act of harm you cannot take back.
Nobody plans to fall off a cliff. You drift toward the edge in steps that each feel fine. An addict is just a man who had one more normal night, a few hundred times. The drive home after two beers is fine, fifty times in a row, until the one time it is not. Getting away with it teaches a dangerous lesson: every trip to the edge that ends well makes the edge feel safer.
I am no angel here. A few times when I was young, I took risks that look foolish to me now. Nothing happened and there is no story to tell, but luck did the work that judgment should have done. Given another chance, I would not roll the dice.
The slowest cliffs don’t feel like cliffs at all. A body you neglect at twenty is a body that punishes you at fifty. No single day does the damage. It adds up quietly, and the bill comes due.
Any number multiplied by zero is zero. It does not matter how much you have built; one bad day at the wrong edge takes all of it. Most of the worst outcomes in adult life come from a small number of cliffs.
The good news is that the cliffs are mostly avoidable. The men who get this right are not braver or more sure-footed than you. They just stay back from the edge. Avoid the cliffs, and be bold about everything else.
Take the Shot
The cliffs punish a single mistake. The shot is the opposite: you can miss a hundred, and one hit pays for them all. Learn to see the shape: small cost, big upside, unlimited tries. Life is full of them.
Take the trip. Throw the party. Ask her out. Apply for the job you do not think you will get. Most of these will not work, and the worst case is almost always the same: you tried, and you felt a little silly for a day. That is a price you can pay every week without going broke.
The big moments of your life will not announce themselves. They arrive on an ordinary afternoon after a small choice. The party where you meet your wife, the trip where you find your city, the class where you find your work — none will seem life-changing at the time. Then one of them is. I met Lauren at a pickup frisbee game.
Be the man who shows up. You cannot schedule luck, but you can give it more chances to find you. It will not find you on the couch. So take the shot.
Learn to Cook
All the big advice above comes down to a cutting board on a Tuesday night.
You will eat every day for the rest of your life. Most men your age hand that decision to a drive-through window and never take it back. Learning to cook is deciding what goes into your body for the next sixty years, and unlike most investments, it pays off the same night you make it.
Chopping vegetables is one of the few activities left in modern life that asks for your hands and your attention at the same time. It is hard to be anxious while you are julienning an onion. No machine in the arcade can reach you at the stove.
Good cooking is mostly preparation. Buy the ingredients, make the sauce ahead, have everything ready before the heat comes on. The sauce does not care that you are in a hurry. That is the same muscle the rest of adult life rewards, and the kitchen will train it a few nights a week.
You will be bad at it for a while. Burnt, bland, sometimes both. Cook anyway. Almost nobody turns down a free meal, and people forgive a bad one faster than you think. Feeding people is one of the oldest ways to find your people.
“Want to make pizza together?” is one of the best things you can say to someone you really like. It is a first date and a fiftieth anniversary in the same sentence. If you marry well, you will cook with the same person thousands of times. Show up, do the work, eat the result, do it again tomorrow.
Your great-uncle Jerry was a bad cook for fifty years. Then he decided to learn, and he spent the rest of his life feeding the people he loved. You do not have to wait that long.
One day, without noticing when it happened, you will be good. You will open the fridge, see what is there, and know what to do. Feed the people you love. There are worse ways to spend a life.
You are eighteen. Between here and eighty there are a little over three thousand Tuesdays. Nobody — not the richest man alive — can buy back a single one once it is spent. That is the wealth you are holding, and nearly all of it is still yours.
Spend it on real things.
I love you, kid. Now go live a life worth repeating.
Chris