37 lessons in 37 years

The second-best form of kindness is to accept someone else’s kindness. Growing up in the south, it was common—and often considered polite—to decline small, friendly gestures. Like, you’re standing in the cold, and someone hands you a hand warmer? “Oh, no, you keep that for yourself.” / “Please, I insist.” / “You’re so kind, but no thank you.” When I learned to accept kind acts and say, “Thank you,” we both walked away happier.

My own growth came from knowing when to bend the rules. Flexibility, like in machines1, makes life resilient. Total discipline is a brittle goal.

Generosity has its own “cash back rewards,” similar to those offered by credit cards. I like giving outsized tips to baristas to brighten their day. On multiple occasions lately, I’ve found $20 bills on the street, as if placed there just for me. A portion of what I give away always finds its way back.

Every time I step out of my door in Manhattan, I’m likely to experience something that puts me to use. Sometimes, a deliveryman drops his boxes and could use a hand picking them up. Other times, someone might need a few extra bucks to cover groceries at the checkout. A few weeks ago, I watched a man step off a bus, lose his footing, and fall. He was clearly embarrassed and waved me away when I offered to help him up. But he accepted my second offer. These little encounters are a near-daily occurrence, and the chief aim is to hone my instincts to be helpful as second nature. I don’t get it right every time, but I’m getting better.

Caring about others’ opinions breeds stress. Letting go of what people think and how they live is freeing, and I’ve found doing so improves my peace of mind.

I put major effort into protecting my inner world. In my head, I’ve evicted the noise of others’ opinions, and I’ve made room for memories with loved ones and hopes I can’t let go of. Good conversations sit on high shelves. Important lessons fill mental notebooks. My inner world can stay peaceful even when the outside world is chaotic.

Belief—in a higher power or even people—is not just a feeling we have or don’t have. Belief is a choice, a bet. So when someone encourages you to “believe in yourself,” what they’re actually saying is: Go for it; take the risk; bet on yourself.

Guilt outlives its use. I’m still bothered by mistakes I made weeks, months, even decades ago, most of which have been rectified. How nice it would be to keep guilt’s lessons without its pain.

My process for dealing with failure: when I fail big, I give myself the rest of the day to feel terrible about it. Maybe I eat sympathy junk food or take a nap. The day is mine to be completely sour and pitiful. But the next day, I move on and get to work.

My most reliable litmus test for big decisions—financial, career-related, and so on—is simple: will this help me sleep at night?

I like the quote by John Bowlby, “Life is best organized as a series of daring ventures from a secure base.”

Ray Dalio said of the current economic climate, “If you worry, you don’t need to worry. And if you don’t worry, you need to worry. Because if you worry, then you’ll take care of the things you worry about. Today, we have the capacity to take care of our problems—if the people involved can rise above their self-interests to deal with them well.”

Seneca gave us a blueprint to know if we’re truly living: look back with joy, look ahead without anxiety, and enjoy today as if it were the last.

Envy has a weird way of showing me what I want in life before I have the language to acknowledge it. It’s embarrassing to admit, but I chose my early career partly out of jealousy, seeing someone else do it first and thinking, “Maybe I can do that, too.”

Holding a grudge is like drawing a small, black smudge on a clean window, then complaining that you can’t see through the glass because the smudge is blocking your view. Life is so much larger than any grudge. There are so many people in the world, so many towns, so many jobs, so many other places to apply attention.

I can’t think of a greater win than enjoying a happy moment as it ebbs and flows. Happiness is hard to find, and even harder to hold onto. A cold gust of wind can blow it away, and word of bad news can drown it. It’s a full-body exercise, so when happiness finds me, I now think of it as a perfect alignment of imperfect, moving parts.

A happy, quiet life looks uneventful from the outside but is its own unique journey—not a stalling of activity, but a slow buildup of potential energy.

Not everything needs to be shared. I wonder if we’ve abandoned the joy of private, unspoken thoughts.

Drinking has never been more than an occasional indulgence for me, and even though I drink in moderation, even a single drink can drag my evening down by a whole letter grade.

Museums used to bore me until I realized the real enjoyment comes from repeat visits.

Being an uncle is incredibly fun, especially with nieces and nephews all in different stages of life. Some of them even think I’m cool.

Movement of all forms has been healthy for me. I’m referring to exercise, of course, but also the act of moving to new cities.

Competence in one’s profession feels like a radical and even righteous act.

This year, I returned to my old hobby of playing guitar, songwriting, and music production. It takes me months, sometimes years, to write a song, and I can’t do it alone—I rely on a small creative circle who’ll give me honest feedback. I’ve noticed that more people are speeding up the creative process with AI and such, but for me, nothing can replicate the feeling of calling a piece of music done after dozens of hours shaping it.

I wrote a novel this year. At the time of writing this list, I’m one month away from completing my third draft. I’m happy knowing that even if it never finds an audience beyond friends and family, I’ve fulfilled a dream I’ve pursued all my life.

Starting the first draft of a novel feels like standing at the base of a mountain and setting off to climb it with broken legs. Good news: you’ll come to “The End” and realize most of the book is written through a steady routine of daily word count instead of constant inspiration. You might have sentences that fell from heaven, but the vast majority of a novel is just showing up each day and filling the page with nouns and punchy verbs.

There’s a quote in the David S. Pumpkins sketch from SNL that I love when thinking about the things I make. “It’s 100 Floors of Frights. They’re not all gonna be winners!”

Speaking of, I’ve learned to grade all things on a curve, getting rid of the phrase, “Nothing is perfect, but…” That seems obvious. If nothing is perfect, then I shouldn’t expect anything to be perfect.

My goal for personal growth is not to stack up habits. Instead, my goal is to add blueprints. I can’t do everything at once—I can focus on health and fitness, but I might need to set my guitar hobby aside to do so. For me, it’s about activating the right habits at the right times.

I’m now on my second career break. The first, in 2020, lasted for ten wonderful months and led to a great new job. Still, as fun as they are, the painful part of career breaks is the loss of that career identity. The freedom is wonderful, but tell that to my ego that misses that fancy title that I might never get back.

(I wrote the previous entry seven months ago, just after leaving my job. Reading it back now makes me laugh because this break has been fantastic.)

My career breaks bring back an old realization—what does one do when their stresses are few and they’re fortunate enough to have health and friends? My answer: make music, write stories, take long walks, and visit friends and family. A simple life doesn’t have to mean a boring life.

As part of my break, I put my phone in a drawer, setting it to Do Not Disturb during the week and powering it down on the weekends. I’m very hard to reach now, missing all calls and returning very few, and I’ve even started to resent any time I have to use my phone, like for Maps or event tickets. After a few months of this, I’ve failed to go back to carrying it around, and I now wish I could get rid of it completely.

People ask me for life advice sometimes, but my advice falls apart. I’ve accepted that most of my success is not my fault.

I’m looking back on my twenties and realizing how much of my success balanced on a razor’s edge. The most impactful events in my life were pure chance, luck, fate, or divine intervention—whatever you want to call it. My ten-year journey from a small town in Mississippi to living in Manhattan seems impossible if I had to do it again.

In Maslow’s Hierarchy of Needs, at the very top, there’s a concept known as Peak Experiences, accompanied by a physical sensation of euphoria, joy, and hope (and not because of substances). They can’t be planned, pursued, or bottled. The body and mind seem to recognize moments when everything is in its right place and reward us accordingly. I’ve had one of these moments every year since 2022. Two were in Central Park in the spring. Another found me while sipping coffee under the shade of the Flatiron Building. The most recent one happened when I sat down to a spaghetti dinner with my wife. Kacey Musgraves’s “Moving Out” played as we ate. Each time it strikes, my fingers tingle, my chest warms, and time slows. It’s an overwhelming feeling of, This is it, this is it.

I have a good life—a great one, in fact. And I’ve come to a time in life when I have something to show for it, gaining not just means, but meaning, and a long list of people who love me. And so, every year offers a new challenge to make the most of it. My life is less, “Is this all there is?” and more, “Look how much there is!”