★★★★★

Highlights

We get ourselves out of the office and into a bar. We have more in common than our grievances, but we kick off by speculating about our job security, complaining about the bureaucratic double-downs, casting blame for blocks and poor product decisions. We talk about our IPO like it’s the deus ex machina coming down from on high to save us — like it’s an inevitability, like our stock options will lift us out of our existential dread, away from the collective anxiety that ebbs and flows. Realistically, we know it could be years before an IPO, if there’s an IPO at all; we know in our hearts that money is a salve, not a solution. Still, we are hopeful. We reassure ourselves and one another that this is just a phase; every start-up has its growing pains. Eventually we are drunk enough to change the subject, to remember our more private selves. The people we are on weekends, the people we were for years.

What is it like to be fun? What is it like to feel like you’ve earned this?

IT’S CHRISTMASTIME; I’m older, I’m elsewhere. On the train to work, I swipe through social media and hit on a post from the start-up’s holiday party, which has its own hashtag. The photograph is of two former teammates, both of them smiling broadly, their teeth as white as I remember. “So grateful to be part of such an amazing team,” the caption reads, and I tap through. The hashtag unleashes a stream of photographs featuring people I’ve never met — beautiful people, the kind of people who look good in athleisure. They look well rested. They look relaxed and happy. They look nothing like me. There’s a photograph of what can only be the pre-dinner floor show: an acrobat in a leotard kneeling on a pedestal, her legs contorted, her feet grasping a bow and arrow, poised to release. Her target is a stuffed heart, printed with the company logo. I scroll past animated photo-booth GIFs of strangers, kissing and mugging for the camera, and I recognize their pride, I empathize with their sense of accomplishment — this was one hell of a year, and they have won. I feel gently ill, a callback to the childhood nausea of being left out.

Lightning bolt
About the author

I'm Justin Duke — a software engineer, writer, and founder. I currently work as the CEO of Buttondown, the best way to start and grow your newsletter, and as a partner at Third South Capital.

Lightning bolt
Greatest hits

Lightning bolt
Elsewhere

Lightning bolt
Don't miss the next essay

Get a monthly roundup of everything I've written: no ads, no nonsense.