36 learnings in 36 years

I told a friend recently that I don’t enjoy celebrating my birthday—I usually prefer the day to pass unnoticed except for a nice dinner and a phone call from my mom. My friend offered a cheeky suggestion: consider aging as “leveling up.” Now, on the other side of my 36th birthday, I’m finding this advice surprisingly comforting.

There are so many opportunities to be kind. Here’s one: buy an extra umbrella. Next time it rains, go out and give that umbrella to the wettest, saddest, umbrella-less person you pass on the street.

I grew up biting my fingernails and spent decades trying (and failing) to quit. Finally, on Christmas Eve, I stopped. I was buying a watch, and the jeweler asked me to extend my hand so he could slip the watch on my wrist. I extended my hand, palm down; then, I instinctively curled in my fingers to hide my chewed-up fingernails from the jeweler. That small moment—curling in my fingers to hide my nails—was when I realized my nail-biting habit was dumb. I haven’t bitten them since.

I feel I’ve achieved moderate success in my career, and it has nothing to do with my morning routine.

Almost anything can be acquired through a strong will or good fortune—anything, except for a time machine.

I’ve decided that as my happiness grows, I should avoid talking about it too much. I’m thinking of the line in the movie Broadcast News. William Hurt asks Albert Brooks, “What do you do when your real life exceeds your dreams?” Albert responds, “Keep it to yourself.”1

When faced with any problem or decision, there are “front-brain” and “back-brain” thoughts. The front-brain thought—the gut reaction, the split decision—comes to you easily, and it’s always a bit wrong. The back brain thought—the one that’s a bit more nuanced and considered—has to be sought out. You can find it in the council of others, in books, or in sweat. Some of my best ideas came to me on a long jog or talking with a friend.

I’ve discovered my key to running long distances: I don’t go home until I’ve hit my distance goal. If I need to stop in the park along the way and sit for twenty minutes, so be it.

I love ChatGPT. It fills my brain’s gaping hole where the math skills should be.2

Buy some Crocs and put insoles in them. Thank me later.

I’ve flossed every night for the past year and a half, but still, during a recent checkup, my dentist told me I wasn’t flossing “the right way.” I realized we’re hard-wired to critique each other, especially when it’s part of our job.

I keep thinking about a line in the show Fleishman Is in Trouble. Two characters are feeling sad about getting older. One tells the other, “I miss longing.” I thought about this line for weeks and realized how enjoyable longing can be if you embrace it. On a superficial level, isn’t shopping for a thing more fun than buying it?

When I ask someone for feedback, I have to remember I’m asking them to invest in my growth without getting much in return. “Feedback is a gift,” after all.

I went to NY Comic-Con last year, and it showed me a sad truth of life: everything is an ad.

Editing your writing over many drafts is crucial because we’re all different versions of ourselves on different days. I start writing these lists in January and edit them for months. The first draft is always a bit cynical and self-aggrandizing. The second draft is more level-headed. The third draft is less judgmental. I continuously edit with the hope that, eventually, I’ll sound a bit less bone-headed.

Nora Ephron once told a great story about her high school journalism class. The teacher gave the class a prompt and asked them to write a lead. The prompt was, “The principal of Beverly Hills High School announced today that the high school faculty will travel to Sacramento on Thursday for a colloquium on new teaching methods. Speaking there will be Margaret Mead, the anthropologist, and two other people.” When the students turned in their answers—most of which were clever rewordings of the original prompt—the teacher ripped up the submissions. He explained that none had arrived at The Point: “There will be no school on Thursday.”3

Letters are a fantastic genre of writing because they’re written in the second person. It’s a story written for an audience of one—you—making it particularly valuable.

TSA PreCheck is worth every penny. Actually, any money spent making air travel more bearable is well spent.

Mosh pits at metal concerts look intimidating but are usually filled with polite people.

I’ve started to put my fears into buckets of “controllable” and “uncontrollable.” Fear of heights, flying, and roller coasters require no control on my part. Turning off my brain is the solution, and I’ve learned to overcome those fears. My fear of public speaking requires a high degree of control—what to say and how to say it—and it took me much longer to overcome.

I’ve tried dozens of wellness practices—yoga, cupping therapy, chiropractic treatments, and more. Those are fine, but nothing beats a restful eight hours of sleep.

“Such that” is my new favorite way to connect thoughts.4

One of the best parts of leadership isn’t having smart people in your orbit—it’s being in theirs. It may sound sentimental, but think about it: we send probes into deep space by using the gravity of larger planets. Likewise, being in the orbit of talented people is key to finding greater opportunities.

It turns out I don’t need a Brita filter. Tap water is fine. Add some ice, and it’s delicious.

If the actions of others don’t make sense, consider that everyone, through every action, is plotting their own freedom.

I decided at some point that most things in my life needed to be drastically simplified—fewer accounts, fewer notifications, a smaller home, limited desk space, three shirts, two pairs of jeans, and one pair of slacks. I meddle with a few things, keeping my mind clear and quite happy.

There are a lot of misconceptions about New York City. For example, I’m told that Manhattan is a violent, scary place where you’re likely to be mugged at any moment, where crime is out of control, and your only hope is to leave. All that is true unless you live here.

“What am I missing?” is a great question to ask oneself daily.

Procrastination can be useful. Most of the work we do in the corporate world is meant to go on forever. Major companies don’t close their doors because their work is “done.” The work goes on, the goals evolve, and leaders come and go. So, it’s okay to occasionally delay that meeting, push that deadline, or “hurry up and wait.“

Everyone is interesting if you’re interested enough to learn why.

Every close relationship exists on a sliding scale from “Student” on one end to “Teacher” on the other. In the middle, there’s “Friend.” It’s important to know where each relationship lives on this scale. I’ve learned that it’s usually a bad idea to become a teacher/mentor to anyone unless asked or paid.

The younger version of me usually entered a room believing he had something to teach the people he found there. But after going out into the world and seeing how the other half lives, it’s more fitting to enter a room ready to listen and learn. There’s so much I don’t know, and that realization has served me well as an adult.

Looking back, I wouldn’t include “Work Hard” in my personal ethos. I’ve always aimed for sustained effort instead of maximum effort. The trick is knowing when to apply bursts of intensity such that5 I don’t burn out or burn others.

Speaking of, I always think about the lesson my dad taught me early on: he took me to work with him at our family’s bark processing plant. After a long, grueling day of shoveling dirt and filling bags with mulch, he told me, “Son, don’t do this kind of work. Don’t work hard. Work smart.” Smart Work, for me, has always been about building strong professional relationships, preserving physical and emotional energy, and, of course, saving and investing my income.

I’ve developed a healthier relationship with that little voice in my head. I’ve decided to root for myself, to retrain my self-talk to be kind and supportive. I’ve learned to forgive myself for mistakes and feel proud when things are going well.

Lastly, I’m counting all the good things. I feel lucky to have a small home in a big city and to have people in my life that I love and wish every good thing for. I’m fortunate to feel at peace—without grudges or ill will—and to have one more day when nothing in life is guaranteed.