The days are long but the years are short

This year, my two cats were diagnosed with cancer in quick succession. Then I learned, quite suddenly, that I only have one year left til I’m 40. It’s enough to put a guy into a reflective mood. Shortly after my first cat passed away (may he rest in the sunny spot), I started jotting down lessons learned. A few thoughts on the eve of middle age:

There is more wisdom in fiction than nonfiction. Most business books are bad. Some are good, but most of those could be blog posts. (And would be but for the economics of books vs. blog posts.) Some history and memoir is truly great, but nothing replaces the afternoons of self-reflection that come from a well-worn Kazuo Ishiguro or Sally Rooney novel.

Nobody cares. Just win. It’s remarkable how hard it is to make an unpopular decision in the moment. Yet nobody remembers how controversial the decision was when the results come in. You’ll be judged by the outcome alone. If you fail, everyone will think you’re an idiot, even if it’s the decision everyone wanted you to make at the time. So just make the decision you know deep down is right, no matter how unpopular it is with the team or the board or anyone else. You’ll be popular when you win. 

It’s the results, stupid. My bigtech friends have internalized the idea that individual outcomes are outside your control, so teams should be measured on how strong and consistent their processes are. They say things like, “the score takes care of itself.” If we’re butchering quotes from football coaches, I prefer, “you are what your record says you are.” I fundamentally don’t care if you won by tripping and falling over the finish line, as long as you won. Here in the real world, we are judged on our results.

Living generously is best. I remember in excruciating detail the times I put myself ahead of others in key moments. I still beat myself up over them. Whatever little gain I eked out for myself in those moments wasn’t worth it. I’m told that when I’m tipsy and happy, I insist on tipping exorbitantly. I don’t know if people tell me that just to butter me up, and I don’t want to ask, because it makes me feel proud to hear it.

It’s so easy to fool yourself into thinking you’re hot shit. You are not. The most important people in my life don’t read this blog on the regular, despite me sending it to them every time I think I’ve written a good one. This is how I know that there is love in my life. A handful of people see me clearly and completely, and yet for some reason love me anyway. Those same people are completely unimpressed by whatever meager professional achievements or social status I think I’ve accrued, and they don’t engage with my silly acts of self-promotion. Professional achievement is good of course, and self-promotion is sometimes necessary, but achievement and attention are not where self-worth comes from.

Big vacations are best after big wins. A long weekend away after hitting $1M ARR. Boarding a flight to Hawaii hours after hitting a big quarter, still wearing the last-day-of-the-quarter suit. Summer in Europe after selling the company. These are some of the most fun, most rejuvenating vacations I’ve ever taken. By contrast, vacations to remedy burnout just make it worse. And vacations just because it’s summer are boring.

To fix burnout, add some joy to your daily routine. I am convinced that Modelbit became a revenue-generating business because, after too long banging my head against the wall joylessly, I bought myself a hipster pour-over coffee setup that makes me smile every morning. Find your daily joy in those little routines for a while. Look forward to them. The joy in the work will come back around as you get personally unstuck.

Eat, drink and travel widely. To be clear, drink as much or as little as you want, I don’t care. My point is, the sensory experiences the world can offer are so diverse. Burn your face off with spice in Southeast Asia. Float in the Dead Sea. Drink Amarula mixed into your morning coffee in South Africa and then drag a bottle through five airports, clutching that Duty Free seal for dear life. Try not to say no to novel experiences.

Cooking for others is an act of service. Cooking with others is an act of trust. To thank someone, to give back to them, to be in service to them – invite them to your home and share a meal you have created for them. To bond a team together with shared trust, rent an Airbnb with a big kitchen and give everyone a task. Watching your head of sales humbly chop vegetables to spec for your head of support is a unique joy that cannot be found anywhere else in the world.

Keep building. There seems to be an epidemic of founders retiring to bigco or becoming VCs after one exit. What a waste of talent. The best thing about technology startups is the opportunity to move the world forward by inches. We do it by inventing the future, and then distributing it widely. What a life. Trading away that life of adventure in the name of a little stability is for other people.

Someday, all you’ll have left are the relationships. For a year or two, every time a senior employee left Periscope’s acquirer, they would bring me a piece of memorabilia from the office, like a cat bringing you a severed mouse head as an offering. Now I have way too much Periscope kitsch, stuffed in a closet that I never look at. And I have my relationships with the team, many of whom are now close friends, bonded by a shared adventure, which I treasure. 

Karaoke is the worst. Every friend group has that one person who could have pursued musical theater but didn’t. They are allowed to drag the group to karaoke a couple times a year, max. OK, maybe more if they’re buying the drinks. And if they'll humor me when I start showing everyone cat photos after the second round.