WHEN YOU'RE HURTING

21. The Habits That Move the Needle

"Happiness is not something ready made. It comes from your own actions." —Dalai Lama

Dear Kids,

I remember the first morning, after a long bad stretch, when I woke up and the inside of my chest just felt quieter — and I made the mistake of asking myself, okay, now what? The sadness lifts and a more interesting question shows up behind it: not how do I survive a bad day, but how do I actually build a happier life on the ordinary ones. That's what this letter is about. Not as a manual but as a series of moments — because the shape of a happier life, in my experience, isn't a checklist. It's a slow rearrangement of small daily choices around the few things that genuinely matter.

Let me start with what happiness isn't.

When I was younger, I thought happiness was a destination — the next promotion, the next Forbes list, the next pint of ice cream after a hard day. I worked for those things. I got some of them. And what I noticed, with a kind of confused disappointment, was that the ice cream was just ice cream, the list was just a list, and the high lasted about as long as it took to refresh the page. What I'd been calling happiness was actually pleasure, or enjoyment, or sometimes just lust dressed up in better clothes.

I now think of happiness, instead, the way the Tibetan Buddhist tradition does — not as a quantity of things acquired, but as a kind of peace with the present. Peace with what you have, with who you are, with where life currently has you. Naval Ravikant says it more pointedly: desire is a contract that you make with yourself to be unhappy until you get what you want. The shorter the list of things you need to be happy, the more often you are. I wrote you once a whole letter asking what you were a slave to in life; this is the gentler half of that same question — not what enslaves you, but what would set you free.

So I'm going to walk you through the habits I've actually found that move the needle, but not as bullet points — I tried that, and the list version of this letter sat in my drafts for months looking exactly like the LinkedIn carousel I would never read. The habits only mean something when you can see the moment that taught them. So here they are, the way I learned them.

The body, on a long flight

I learned the first habit late, the hard way. There was a long stretch of my mid-twenties where I treated my body the way a startup treats a server — push it harder, ignore the alerts, restart it with coffee, repeat. I drank when work was stressful, which was most of the time. I slept five hours and called it discipline. I sat for ten-hour stretches and called the stiffness in my back "just getting older."

The turning point wasn't dramatic. It was a long flight, somewhere over the Pacific, where I stood up to use the bathroom and felt every joint in my body grind in a way that twenty-six-year-olds are not supposed to grind. I sat back down and thought, very clearly: I am doing this to myself.

So now I treat the basics like they're load-bearing, because they are. Eight hours of sleep, on a consistent schedule. No alcohol if I can help it — I lost taste for what it did to me. Less sugar, less processed food, less caffeine after morning. Stretching. Walking. Standing up every hour. Confucius wrote that a healthy man wants a thousand things, a sick man only wants one — and you don't fully feel the truth of that line until you've had a week where the only thing you wanted was for your back to stop hurting.

The other piece of this, the part that surprised me, is that movement is better when it's social. I started playing pickleball — I know, I know, the most thirty-going-on-sixty sport on earth — and it does more for my mood than any solo gym session ever did. Sweat plus laughter plus people you genuinely like is a chemistry I haven't found anywhere else. So that's the first habit, two for the price of one: take care of the body that's carrying you around, and find a way to move that involves other humans.

The supermarket line

The second habit I learned in a supermarket, of all places.

I was in a checkout line behind a mother with two screaming kids, at the end of a long day, and I felt the familiar pull of "today is terrible." Same exhausted body, same fluorescent lights, same five-minute wait. And it occurred to me, almost involuntarily, that I had a choice about the next thirty seconds. I could be the guy thinking my day sucks — and I'd be right, because the world reliably reflects back the lens you bring to it. Or I could be the guy thinking I'm somehow lucky enough to be standing in a heated grocery store with food I can afford and a body that works — and I'd also be right.

I don't always pick the second one. But I pick it more often than I used to. Viktor Frankl, who watched the worst of what humans can do to each other from inside a concentration camp, wrote that between stimulus and response, there is a space. In that space is our power to choose our response. In our response lies our growth and our freedom. That sentence is the second habit. Build the half-second of space between what happens and how you respond. Use it.

The cousin habit to this — the one I'm worst at — is staying out of arguments I don't need to be in. Younger me felt I had to be right in every conversation, even with people whose opinion I shouldn't have cared about. Keanu Reeves, of all people, captured the antidote: 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. Letting people be wrong on the internet is a meditation practice. I'm still in the early grades.

The Eleven Madison Park dinner that wasn't quite worth it

The third habit is about money, which is also about happiness, but only up to a point — and the point is much closer than the world suggests.

Kahneman and Deaton famously found that day-to-day happiness rises with income up to about $75,000 a year (in 2010 dollars), after which it plateaus. The number isn't sacred, and the line moves with inflation and where you live, but the shape is the important part: a curve that flattens. Money buys you out of the worst sources of stress — bad housing, food insecurity, untreated illness — and then it mostly stops buying anything that affects your mood for more than a week.

I tested this against my own life by going to Eleven Madison Park once. It was an extraordinary meal. I want to be honest: it did not change anything about my life. The food was beautiful, the company was beautiful, and the next morning I was the same person I'd been the day before, with a slightly lighter wallet and a slightly heavier stomach. Tasting menus do not appear anywhere in Maslow's hierarchy. They are nice. They are not happiness.

The phenomenon underneath this has a name. Researchers call it hedonic adaptation — the human tendency to return to a relatively stable baseline of happiness no matter what happens to us, good or bad. First week after winning the lottery: HELL YES. Five years later: eh, fine. They found the same effect, more sobering, in negative events — people who lost limbs returned, on average, close to their previous baseline within a couple of years. The mind is a thermostat. It corrects.

The other thing money does, which we forget, is that it has a brutal discount rate. At twenty, you might trade five years of your life for a million dollars. At ninety, you would happily pay a million dollars for five more weeks of good health. Plan your life knowing the exchange rate flips on you.

The energy vampires

The fourth habit took me embarrassingly long to learn.

You are, as I keep telling you, the average of the five people you spend the most time with. Show me your friends and I'll show you your future. And yet for years I kept around people who left me drained — what I came to call the energy vampires. The persistently negative ones, the chronically dramatic ones, the ones whose calls I'd see come in and feel my shoulders tense before I'd even picked up.

In my younger days I was convinced my own optimism could fix them. I entered relationships and friendships alike with the project-management attitude of I can fix this person. Narrator, as I once wrote elsewhere: he did not fix anything. He just got tired, slowly, and then all at once.

The harder, less-glamorous version of this habit is the inverse: actively spending time with the people who are kind, curious, generous, and a little bit weird in the directions you admire. The friends you walk away from feeling more like yourself, not less. Reconnect with old friends. Be the one who texts first. Send flowers when there's no occasion. Tell people you appreciate them, plainly, in words that are slightly embarrassing — because the embarrassment is the data that the sentiment is real. Stay up until the sun rises with someone you love, once a year, on purpose.

Angelo's question

The fifth habit is the one I'm still figuring out, and I learned it from my friend Angelo over dinner.

Angelo asked me, mid-bite, do you believe in God? I braced for a theological debate — I'm the kind of person who can argue any side of this for hours and end up convincing no one, least of all myself. But Angelo wasn't actually asking about theology. He was asking about gratitude. His point was this: having something larger than yourself to rely on — God, the universe, the universe's tendency to provide, whatever you want to call it — means you can take your hands off the wheel sometimes. You don't have to carry the full weight by yourself. You can trust that things, eventually, will work out.

When I was younger, I was certain about everything. No higher power, pure rationality, white-knuckled grip on every steering wheel I could find. I thought my anxiety was just a sign that I cared. What Angelo handed me, over a plate of food I no longer remember, was a different way of holding the wheel — looser, with more faith in the road.

So the fifth habit is gratitude as a daily practice, even when nothing in particular is going right. I keep a journal. Some days the entry is a paragraph; some days it's three lines. The point isn't the writing, it's the noticing. What was good today that I almost missed? Who was kind to me today? What did my body do for me today that I didn't thank it for? It is impossible to be genuinely grateful and chronically anxious at the same time. The wiring doesn't allow it. You can verify this on yourself.

The Stoic on the nightstand

The sixth habit lives on my nightstand: a small stack of books I keep coming back to. Marcus Aurelius's Meditations. Viktor Frankl. The Tao Te Ching. A few of the older Buddhist texts. I'm not religious in any organized way, but I've come to think of these as load-bearing walls for the mind — the kind of writing that holds you up when your own thinking won't.

The thing I love about the Stoics specifically is that they were writing for themselves, in private, about how to be less reactive and more present. Marcus Aurelius was an emperor scribbling reminders in the margins of an empire, and most of those reminders are versions of calm down, this isn't as big as it feels. When I get worked up about something — a meeting that went sideways, a person who was unkind, a missed flight — five minutes with one of those books is usually enough to right me. It's cheaper than therapy and more portable than a friend.

The companion book on that nightstand, the one I open when I don't have the patience for Marcus's longer passages, is Ryan Holiday and Stephen Hanselman's The Daily Stoic — one page per day, one passage from the ancient Stoics with a paragraph of commentary. I started reading it during a particularly chaotic stretch building Skylarq — the months when Jack and I were on daily syncs and every conversation felt like triage — and the daily-page format turned out to be the right size for an exhausted brain at the end of a long day. The lesson I keep taking from it isn't any single passage — it's the fact that the people writing about how to be calm and present two thousand years ago were dealing with the same dumb stuff I'm dealing with now. Petty colleagues. Anxious egos. The tug of approval. There is no new emotional weather. There's just whether you've practiced enough to sit with it. Reading one short page a day is a way of practicing.

The sister habit is talking to people older and wiser than me. I've learned to seek them out actively. Most of the best advice in my life has come from a meal with someone in their sixties or seventies who has already lived through the shape of the decade I'm currently afraid of. Their fears, in retrospect, were almost never the right fears. That alone is worth knowing.

Remember you will die

The last habit is the strangest one, and the one I most rely on.

I remind myself, often, that I am going to die. Not in a morbid way — in a clarifying way. The Stoics called it memento mori. The Tibetans built whole meditation practices around it. The basic move is: you imagine yourself, at the end of your life, looking back at the choice you are currently agonizing over, and you ask whether it's going to matter.

Almost nothing does. The work email I'm anxious about, the slight from a colleague, the LinkedIn post from someone whose career suddenly looks better than mine. From the deathbed view, all of it dissolves. What's left is the people I loved well, the small kindnesses I performed without needing credit, the things I built because I genuinely wanted to build them, the moments I was actually present for instead of mentally somewhere else.

This is the habit that ties all the others together. Take care of the body, because it's the one you have, and the meter is running. Choose your response, because the seconds count. Don't sacrifice your life for money that won't taste like much when you have it. Spend time with people who light you up, while they're still here. Be grateful, because the alternative is wasting the time you have on resentment. Read the old books, because they were written by people staring at the same fact you're staring at. Remember you will die, because forgetting is what makes ordinary life feel small.

The counterargument I owe you

I owe you the honest counterargument, because the voice in your head will eventually raise it. Someone will tell you that all of this happiness-as-a-skill talk is a privilege — that gratitude journals are easy to keep when you have shelter and food, that "choose your response" is a thinner sentence in a body that's chronically ill or a mind that's depressed, that not everyone gets to walk away from the energy vampires because some of them share your last name.

That voice is partly right. There are real, biological reasons happiness can become temporarily inaccessible — depression, anxiety disorders, the chemistry of grief. Nothing in this letter is meant to trivialize that, and if that's where you are, the right answer is a real doctor and real medication and real time, not a thirty-something father's bullet points. I'd rather you read this on the ordinary Tuesdays.

But the deeper version of the objection is wrong, and I want to say so clearly. The fact that some circumstances make happiness harder doesn't mean it isn't a skill — it just means the skill is harder for some people than others, the same way running is harder if you start with a heavier load. The training still works. The space between stimulus and response still exists, even when it's smaller. Frankl found that space in a death camp. I think I can find it in a supermarket line.

So that's the letter, kids. Move your body, find sport you do with friends. Build the half-second between stimulus and response. Don't expect money to do work it can't do. Get the energy vampires out, and tell the good people you love them. Practice gratitude. Read the old books. Talk to the old people. Remember you will die.

None of these were on a list when I learned them. They were dinners, and supermarket lines, and a long flight, and a friend named Angelo asking a question I didn't expect. Your version will be different. That's the whole point. You'll have your own Angelo, your own supermarket, your own long flight. Pay attention when they show up.

Any other things you've found that have helped make you happier? Please let me know. I'm still learning this one.

Love,

Dad.

Postscript