On shedding the old self like a snakeskin

Hiring and firing, bankruptcy and fundraising— none of that is supposed to happen in your bedroom. Is it so bad to outgrow a place, a person, or a chapter of your life?

When I made the (not universally popular) decision to leave New York City for a small, suburban beach town, I got a little bit of the “wherever you go, there you are” type of feedback. Grown-up life, it was implied, is always complicated, harried and hectic. There will always be water damage and broken heaters and supers with bad attitudes who don’t respond to your calls.

That might be true, and I might have been running from specters that will reappear with new names and faces in yet another zip code. To some extent, whenever you hand in your old troubles, you are simply trading them in for new ones, which will eventually grow old and ripe for the trade-in as well.

Well— sort of. Is that even true?

I had lived in the same zip code from 19 to nearly 32, which I think is fair justification enough for wanting to move. But there’s more to it that— and I’m sorry to say it, I’m sorrier still to sound snooty about it— I don’t think the uninitiated would understand.

I’m not sure I myself understood until my last week in Brooklyn, on an uncharacteristically sunny morning spent walking laps around the McCarren Park track with my friend Kim of the Internet.

I moved into my apartment less than a year into my founder journey. I committed to it sight unseen, despite the fact that my broker told me over and over again that it wasn’t in very good condition, and the ownership really cut corners on installing things or fixing what was broken. It was Covid, I’d just spent a long time living with my parents, and I was desperate— this felt like my last and only chance to rejoin life as a young person, to start this entrepreneurial chapter as an adult, to prove to everyone just how capable, driven, and discerning I was. I had to have the apartment.

Once I had it, I needed it to be a scion of my good taste as an adult. I was 27 or 28, and I was spending way too much time researching how to import Italian chairs. Never mind that the apartment was way too big for one person, that I had no income whatsoever as a founder, that I was a single woman with no resources living alone after a pandemic— I bit off way more than I could chew. Visions of a house packed with glamorous friends, colleagues, and a handsome husband that I hadn’t met yet¹ danced in my mind. Never mind that in all those visions, the “me” that I saw wasn’t anything like who I was now. I ignored that part and focused on sourcing a $2,000 “sustainable” Parachute mattress that I couldn’t afford.

When it arrived and I slept on it on the ground, I sort of hated it. It was a bit of a metaphor for how I felt about running a sustainable marketplace, which I wasn’t really credentialed to do. What the hell did I know about sustainability, besides being reasonably passionate the US should uphold the Paris Agreement? What the hell did I know about supply chain and making something sustainable, really?

But I was 28 and thought I knew mostly everything, everything that mattered, anyway.

I kept the mattress, added the $2,000 to the stack of mounting credit card debt, and wheezed and panted while I shoved it into “the guest room.” I ordered a mattress I actually liked from Amazon instead, promising to myself that this one un-sustainable purchase was inconsequential, and when it arrived I struggled to get it up the stairs by myself, and slept well for the first time in weeks. (Ominous foreshadowing…)