
I turned thirty-three last week, a few days before I leave the country for the better part of a year, which means I have been doing my reflecting surrounded by cardboard boxes and the particular smell of an apartment that no longer recognizes you. Most of my life is in storage or on my back. The rest is being notarized.
I have never been good at birthdays. Not in the depressive way, just in the sense that I never knew what they were for. There are usually celebrations around the day, and those I enjoy fine. But the day itself I have come to observe in the manner of Ron Swanson: I buy myself a good steak, pour a scotch, and put on Bridge on the River Kwai or something else with men building or destroying something at great cost. No party. A quiet, slightly grim ceremony of one. It turns out this was closer to the right instinct than I knew.
So this year I went looking for a better way to hold the thing, and I ended up, as I tend to, with the Stoics, who had opinions about almost everything and were rarely cheerful about any of it.
Here is what surprised me. The Stoics did not really do birthdays as celebration. Seneca, who could find the shadow in a sunny afternoon, treated each passing year as a portion of life already handed over to death. Not "another year older," but "another year spent." The candles aren't marking what you've gained. They're counting down what's been withdrawn from the account. Every birthday is a small, frosted memento mori with your name written on it in gel icing.
I find this oddly comforting, which probably says something about me I should examine on a different week.
Because the Stoic birthday isn't a party. It's an audit. You sit down with the year and you go through the ledger, and the only honest questions are the boring ones. What did I actually do with the time. What did I tell myself I was doing. Where do those two stories disagree, and which one is lying.
I did that audit. I will spare you the line items. But the headline finding, the thing that genuinely caught me off guard, is what is no longer in the books.
For most of my adult life I carried a low background hum of guilt about the things I was supposed to have by now. You know the inventory. It gets handed to you so early you mistake it for your own idea. By thirty-three you are meant to have the partner and the kids, or at least the mortgage and the dog as a down payment on them. The title with enough syllables that strangers nod. The square footage. The retirement account fat enough to prove you took the future seriously. I have eight years in recruiting, which means I spent a good chunk of my career professionally adjacent to other people's ladders, watching them climb and helping them climb and quietly wondering when I was going to start.
I don't have those things. I have two laptops, a contemplative practice I have been running for fifteen years, a newsletter, a piece of software I built so it could keep working while I disappear, and a one-way-ish flight.
And the guilt is gone. That is the part I want to be careful about, because the easy version of this sentence is a lie, and it's the specific lie I find most tedious in other people. I have not transcended desire. I am not writing to you from some serene plateau above the petty human hunger for stability and status. If I told you I no longer care about any of it, I would be performing the exact frictionless non-attachment that makes me want to leave the room.
The truer thing is quieter and a little stranger. The guilt didn't get resolved. It got quiet. And I noticed its absence the way you notice a refrigerator that has been humming for years only in the silence after it finally stops. One day you realize the sound is gone and you cannot remember when it left.
Some days that silence feels like relief. Some days it feels like a smoke detector with a dead battery, and I catch myself thinking: should I be more worried that I'm not worried? Is the absence of the alarm a sign that the house is safe, or that the alarm broke? I genuinely do not always know. That uncertainty is, I think, the actual condition of redefining success, as opposed to the LinkedIn version where someone announces they've redefined success and attaches a sunset.
You don't get to finish the redefinition and then live inside the clean new version. You live inside the redefining. It's a verb, not a destination, and it's a lot less comfortable than having a creed. I cannot hand you my new definition of a life well spent because I am still in the middle of writing it, and the draft is messy, and parts of it are clearly going to get cut.
And I don't think I'm alone in the middle of that draft. This is the part I keep circling back to, because it would be easy to make this a story about one slightly unusual person packing up his apartment, and I don't think that's what it is. The guilt got quiet for me, but I suspect it's getting quiet for a lot of people at once, which is a stranger and more interesting thing.
We were handed a deal early. The terms were simple and almost never spoken aloud: give us your twenties and thirties, your attention, the good hours of your best years, and in exchange you get security and comfort and a story that makes sense. Sell the soul, keep the house. For a while the deal more or less paid out, which is why nobody examined it too closely. But the payouts have gotten thinner and less reliable, the layoffs arrive regardless of how much soul you handed over, and the house, if you can still afford the house, no longer feels like it was worth the trade. A lot of people are looking at the contract for the first time in good light and noticing it was never actually a fair one. We just couldn't see the terms clearly until they stopped being honored. The lie doesn't work anymore, or it works for fewer of us, and the noticing is happening everywhere at once.
So when I say the guilt is gone, I don't think I'm describing some private spiritual achievement. I think I caught an early train on a route a lot of people are about to be standing on the platform for.
What I can tell you is what I'm doing with the absence of the old definition, which is leaving.
In a few days I get on a plane to Mexico City, and from there the route runs south through Central America and down the spine of the continent, then across to South Africa, then east through Southeast Asia and down to the bottom of the world, before it loops home in December. Six and a half months. Solo. I have been to more than thirty countries, spent a month in Peru, did a semester at sea on a cruise ship that turned into a floating classroom, and once spent a summer living in Rome guiding tourists around Europe, so this is not my first encounter with the disorientation of a place that does not run on my assumptions. But it is the first time I am doing it without a return slot to fall back into. There is no job holding my chair warm. There is no chair.
I have spent the last few years quietly building the apparatus that makes this possible, and I want to be understated about this part because it is the part most likely to curdle into a pitch, and a birthday meditation that turns into a pitch is a sad little artifact. So briefly: the work I do now does not require me to be anywhere. The newsletter you are reading is part of it. The software is part of it. There are a few other experiments in keeping the lights on that don't depend on a single employer deciding I'm still worth the seat. None of it is guaranteed. Some of it may not survive contact with seven months of unfamiliar wifi and my own ADHD-shaped relationship to consistency. I am genuinely not sure the work holds together once you remove the apartment, the routine, the fixed blocks of a stationary life. That's sort of the experiment. You cannot find out whether the scaffolding was load-bearing until you take it down.
There's a version of this that sounds brave. I don't experience it as brave. I experience it as the most honest available response to an inventory that kept coming back showing the same result: the things I was supposed to want, I had stopped wanting, and the wanting had not been replaced by panic. Just by a kind of curiosity about what's actually out there once you stop arranging your life around the fear of not having the standard furniture.
Seneca, in one of the letters, says something about how the point is not to live long but to live enough, and that a life is complete whenever you make it so, the way a story is complete whenever it's well told regardless of length. I am not going to pretend I've made mine complete. At thirty-three the more accurate statement is that I have finally stopped trying to live somebody else's version of it, which is not the same as having figured out my own.
But it's a start. And the boxes are packed. And the plane leaves Friday.
I'll write to you from the road.