I’ve exited four tech jobs in ten years, and most of the work I did in each has since been wiped away. The websites I built have been replaced, the features I added have been deprecated, and the teams I managed have been dissolved. But none of that really matters to me anymore; my greatest takeaway from those jobs is the growing list of former coworkers I can email out of the blue just to say hello.
Don’t talk too much about your old job at your new job. Even if it’s completely relevant, even if you were hired for your past experience, starting a sentence with, “In my last role…” will annoy your new coworkers.
If you live in an expensive city, don’t tell people how much you pay for rent. It’s guaranteed to upset them.
Firsthand discovery: work won’t love you back.1
Secondhand discovery: a man, through his choices, might come to the end of his life long before he’s dead.
Mantras are important. A small voice comes to my mind often that says, “This is your life.” On good days, the voice sounds grateful. On bad days, the voice sounds like a warning.
I’ve given up being angry at anyone about anything. My worldview softened when I started telling myself each day, “I will resist the urge to be angry; I will judge no one, speak ill of no one, and cast no blame.”
The thrill of sending long letters, whether handwritten or typed in an email, has become clear over the past year. I’ve sent dozens of them—some short, most long—to pass along good wishes, offer condolences, or make peace where it’s warranted. People tend to write equally long responses, and they’re always lovely to read.
Giving big tips is always appreciated. I’ve also started leaving little notes in the “Special Requests” section on online food orders. Instead of “Extra cheese,” I’ll write, “You’re the best,” and I’ll see smiley faces drawn on the receipts next to my message. I’ve been doing this for a few months, and there's now a Mediterranean restaurant on 6th Avenue that gives me free lemonade every time I stop in.2
In the investing world, there’s growth, and then there’s capital preservation—taking on less risk to avoid losses. So it goes with life: I think there’s a time for growth and hard work. But I also think there’s a time for slowing down, sleeping more, eating well, and daily reminding yourself these are the good days; these are the good days.
Vigorous exercise defeated my years of relentless hypochondria.
Critiquing how other people live their lives is not worth the time or effort.
I appreciate this quote by Scott Galloway: “Your job can be the ink in your pen, but it's not your story.”
If you’re visiting a restaurant and the waiter offers you bread, always say yes. Never, not once, not a single time have I ever regretted getting bread.
For years, I’ve been adding “stars” in Google Maps on almost every place I’ve visited around the world—restaurants, hotels, stores, attractions, airports, and more. I’ve saved over 700 locations worldwide, and I love my star map the same way others love collecting stamps or coins.
Whenever I’m weighing a big decision, I consider: to what end?3 This always helps me reverse-engineer my choices and realize the end might not justify the means.
The world is as dangerous as you think. The world is as safe as you think.
The greatest privilege is working because you want to and not because you have to. My career sabbatical in 2020 taught me that I don’t need a career to feel fulfilled. So, unfortunately for my current and future employers, I now know I can simply walk away from a job at any time if the mood strikes me, and I’ll probably be just fine.4
Leisure made me feel bad until I realized I was just bad at leisure.
Growing up means buying three essential items: 1) a white noise machine to drown out the neighbors and their loud music, 2) a humidifier to help with dry skin and seasonal allergies, and 3) a bidet because toilet paper is getting expensive.
Two notes about happiness: it doesn’t have to be on display (on social media) to grow, and it’s easily spoiled when it depends on the actions of others.
After years of research and changing tastes, I’ve concluded that Howl’s Moving Castle is my favorite Studio Ghibli movie. Honorable mention: Kiki’s Delivery Service.
Anyone who thinks they’re too smart to be manipulated hasn’t lived with a cat.
On the upper floor of the Museum of Modern Art in New York City, there’s a tall window where you can overlook an outdoor courtyard surrounded by classic city architecture. When I first looked out that window, it had such an effect on me that I wondered if the museum had made a huge mistake putting it there. The art I’d paid to see was suddenly less engaging. A person looking out that window, already feeling some sort of artistic reverence, can only think about how expansive New York City is and how nothing else man-made even comes close in comparison.
I’ve started judging my quality of life by how I feel on those rainy Tuesday nights when there’s nothing to do and nowhere to go. On those nights, life feels stripped down to essentials.
In California, my wife and I lived without a dishwasher or air conditioning for over five years. I’ll never again take those luxuries for granted.
I’ve obsessively tracked our net worth and spending habits for years now, and it’s given me a tremendous feeling of control and confidence in our finances.
Good leaders lack two things: ego and greed.
I like Nora Ephron’s movies, and I like her books and essays even more.
My favorite reading hack: listening to audiobooks while playing video games on mute.
I’m a picky and infrequent drinker—bourbon only, no more than one drink per week, and only if I’m in a good mood before the first sip. Here’s my Old Fashioned recipe: 1 teaspoon water, 1 teaspoon maple syrup, 2 dashes of Angostura orange bitters, and 2 ounces of Bulleit Bourbon. Squeeze and drop a Luxardo maraschino cherry into the glass. Add ice. Stir until cold. Enjoy with a friend.
The ability to have difficult conversations early and often is one of many keys to a better life.
I’ve learned to better appreciate my body. My large nose can suck in so much air when I run. My droopy posture makes it easier to bend down and kiss my wife. My elevated cholesterol is something I share with my dad, and I certainly wouldn’t trade him for lower cholesterol.
This year, with this list, I’m capturing a moment when my life feels abundant, lacking nothing. I’ve somehow crossed that line from seeking purpose and meaning to relishing self-actualization. It feels terrific. I know life will take its turns and this feeling is delicate, but for now, I’m reminding myself that these are the good days; these are the good days.
See also my lists from 31 and 33.
Sarah Jaffe wrote a great book about this.
They tell me I’m their favorite customer, too.
This is similar to the “ask why five times” realization I had last year (#13) but more efficient.
Dear current employer: don’t worry. I’m not going anywhere.
I look forward to these every year. I reckon I need to work one of these up for Mark as Read. Yours is very chill and mine probably will be more shrill. Need some of your yoga zen.