◆ To My Future Kids Phillip An

WHEN YOU'RE BECOMING YOURSELF

5. What Are You a Slave To in Life?

"You are free in inverse proportion to the number of people to whom you can't say 'fuck you'. But you are honorable in proportion to the number of people to whom you can say 'fuck you' with impunity but don't." —Nassim Nicholas Taleb

Dear Kids,

Kiddos — what, exactly, has quietly taken ownership of your life? Not in some abstract philosophical sense. The actual thing. The one whose absence would be intolerable. Sit with that for a second before you keep reading, because the rest of this letter doesn't work if you don't.

I was working out the morning I first really sat with this question. I had Seneca's Letters from a Stoic open on my phone between sets, which is admittedly an absurd image — a sweaty twenty-something in a gym reading a Roman senator's mail — and I had to put the weights down and just sit with the page. The line that stopped me was this:

Only an absolute fool values a man according to his clothes, or according to his social position, which after all is only something that we wear like clothing. Show me a man who isn't a slave; one is a slave to sex, another to money, another to ambition; all are slaves to hope or fear. I could show you a man who has been a Consul who is a slave to his 'little old woman,' a millionaire who is the slave of a little girl in domestic service. […] And there's no state of slavery more disgraceful than one which is self-imposed. What is the good of having silence throughout the neighborhood if one's emotions are in turmoil?

I read it three times. I sat on the bench with the dumbbells at my feet and read it again. Two thousand years ago, in a different language, on a different continent, a man with no internet, no advertising, no social media — and he had us nailed.

Because here's the thing Seneca understood that I had to learn the slow way. You will be a slave to something. The architecture of being human, as far as I can tell, doesn't allow for a master-less life. Even people who think they're free are usually serving an unexamined desire — money, status, comfort, approval, a particular kind of attention, the next dopamine release from a glowing rectangle in their hand. The choice you have isn't whether to serve. It's what.

So what is it for you?

Sit with that question for a minute before you keep reading. Not the abstract version. The actual one. What, in your life right now, is the thing whose absence would feel intolerable?

Is it status — the need to be visibly impressive in the eyes of people whose opinions you wouldn't actually trust on anything else?

Is it the desire to be loved — and underneath that, the deeper desire to feel finally and unmistakably enough, so that you can stop performing for the audience inside your head?

Is it money? Comfort? The car, the house, the watch, the version of yourself that exists in photographs?

Is it achievement — measured in titles, in followers, in promotions, in the steady accumulation of badges that prove you're not falling behind?

Is it substances — alcohol, sugar, caffeine, weed, the small chemical permissions you give yourself to feel okay?

Is it the slot machine in your pocket? The infinite scroll? The dopamine drip your brain has gotten used to and now expects, the way it once expected food?

Or is it something quieter — your own reactivity? The unexamined emotions that hijack you at the slightest provocation? The way a careless comment from someone you barely know can ruin your afternoon? The need to be right in every conversation, even with people whose opinions you don't respect?

There's no shame in the list. The shame, Seneca would say, is in not noticing. The most disgraceful kind of slavery is the kind you don't realize you've signed up for.

Oliver Burkeman makes the brutal version of this point in Four Thousand Weeks, which I read in Spangler one rainy afternoon during my second year at HBS, in the slack hour between a case discussion and a study group, and have been mentally arguing with ever since. His thesis is the math itself: if you live to eighty, you get roughly four thousand weeks on this planet. Not years. Weeks. He spends the rest of the book demolishing the productivity industry's promise that with the right systems and apps, you can finally do it all. You can't. You will never do it all. The to-do list is not a problem to solve; it is a description of being mortal. The slavery Burkeman names — and the one I caught myself in immediately, with my color-coded calendar and my five productivity apps — is the slavery to the idea that eventually you'll get on top of things. You won't. And the energy you spend trying to is its own master. The freedom isn't in finishing the list. It's in choosing, on purpose, which fraction of the list you were ever going to do, and letting the rest go without guilt.

Naval Ravikant has the cleanest modern formulation of what Seneca was getting at, and it's a sentence I think about almost weekly:

Desire is a contract that you make with yourself to be unhappy until you get what you want.

Read that twice.

Every desire is a self-imposed contract. You're betting your present peace on a future condition. I will not be okay until X happens. And the cruel mathematics of it is that even when X happens, your brain almost always invents X+1 within a week. The promotion you needed becomes the promotion after that. The number in the bank account that was going to make you finally feel safe becomes a larger number that you now need. The relationship that was going to complete you starts to feel insufficient the moment you have it. This is hedonic adaptation, and it is one of the most brutally efficient pieces of machinery in the human brain.

This isn't a reason for despair, by the way. It's a reason for design. If every desire is a contract to be unhappy, then the question of which desires you let yourself sign — which masters you serve — becomes one of the most consequential design choices of your whole life. Choose carelessly, and you spend decades chasing things whose acquisition won't actually change how you feel. Choose carefully, and the slavery starts to look more like devotion.

Erich Fromm, in To Have or To Be?, gave me the cleanest vocabulary I've found for the split underneath all of this. He divides our two basic modes of existence into having and being. The having mode is the one most of us default to without realizing — life as accumulation, where the question is always what do I own? what do I have on my CV? what experiences have I collected? what does my LinkedIn say about me? The being mode is something else entirely. It's life as presence — what you are doing right now, who you are with, what you are becoming. I came across Fromm in my mid-twenties and felt slightly insulted by how accurately he described the version of me who treated everything, even the people I loved, as something to have rather than something to be with. The shift from one mode to the other is harder than it sounds. You can't will it. You can only notice, again and again, which mode you've slipped into — and choose, when you catch yourself, to put the having mode down for an hour and try the other one.

The good kind of slavery

Because I don't want you to read this and conclude that the answer is monk-like detachment. It isn't. Unless you're going to fully commit to a monastic life — and most of us aren't — you are going to be a slave to something. The question is just whether it's something worth the price.

Everything we romantically call passion and love and art and purpose — every single thing that makes the heart flutter, that brings you to tears, that makes you say this is what life is for — every one of those things is, in Seneca's framing, a form of slavery. You're contracting your present peace against a future condition. You're letting something outside yourself dictate how you feel.

The difference is that these are masters worth serving. A cause that saves lives. A craft you spend forty years deepening. A love that survives wars and pandemics. A child you would die for. These are the contracts I want you to sign with your eyes open, deliberately, knowing what they cost — because the alternative, a life with no masters at all, isn't freedom. It's just emptiness with no traction.

So the mission isn't to escape all the contracts. It's to pick a small number of them worth the price, and to decline the rest as cheerfully as you can.

Premeditatio Malorum — preparing to lose everything

Seneca had a strange practice I want to tell you about, because it sounds extreme until you try it.

He recommended that you periodically practice not having the things you're a slave to. Dress in rags for a few days a month. Eat plain food that would make prison rations seem like a feast. Sleep on the floor. Meditate, in real and specific detail, on losing the people you love. Not because suffering is good — he wasn't a masochist — but because the things we cling to most desperately turn out, when we actually try going without them, to be much less essential than we imagined.

Everyone faces up more bravely to a thing for which he has long prepared himself, sufferings, even; being withstood if they have been trained for in advance. Those who are unprepared, on the other hand, are panic-stricken by the most insignificant happenings. We must see to it that nothing takes us by surprise. […] Until we have begun to go without them, we fail to realize how unnecessary many things are.

The technical name for this is premeditatio malorum — the premeditation of evils. The practical version, for our era, is something like this: when you find yourself afraid of losing something — a job, a relationship, a level of comfort — sit with the specific, granular reality of what life would actually look like if you lost it. Not the catastrophic fantasy. The actual day-to-day. Most of the time, the loss is smaller and more survivable than your fear of it. And once you've seen that, the thing has less power over you. You can hold it more lightly. You can serve it less.

This is the move that turns a slave into a free person. Not running away from what you love, but knowing — really knowing, in your gut — that you would be okay without it. From that place, you can love it without being owned by it.

The unexamined life is the self-imposed cage

There's one more form of slavery I want to flag for you, because it's the one I most often see in people my age and I most regularly catch in myself.

It is the slavery of needing to react.

Someone says something thoughtless. Someone misreads you online. Someone less competent than you gets credit for something. The whole day, gone — replayed, re-litigated, the imagined comebacks rehearsed in the shower. By reacting, by giving the comment weight, you've handed them a piece of your peace. They didn't ask for it. You volunteered it.

Keanu Reeves has a line that I quote to myself probably once a week:

I'm at that stage in life where I stay out of discussions. Even if you say 1+1=5, you're right — have fun.

I love this because it isn't aloof or dismissive. It's a recognition that your finite attention is one of the most valuable things you own, and that defending yourself against opinions you wouldn't even respect is one of the most expensive things you can spend it on. Most insults don't deserve a response. If the person isn't someone whose judgment you trust, why are you giving their judgment power over your day?

Socrates, two and a half thousand years ago, said the unexamined life is not worth living. I think part of what he meant was this. If you don't examine your reactions, the world will choose your masters for you. The traffic will master you. The stranger on the internet will master you. The careless coworker will master you. And then, at the end of your life, you'll look back and discover that you spent your one short pass through this world being yanked around by people and circumstances you barely remember.

I don't want that for you. So examine. Choose. Decline cheerfully. And every so often, when you find yourself unhappy, ask: what am I a slave to right now? Is it worth the price?

If yes — pay it gladly. If no — let it go.

Either way, the choice is yours. Which is the whole point.

Love,

Dad