This is the second dispatch of Justin and Jasdev’s penpal newsletter, Letters to J.
You can read the first here.
(Justin ⇒ Jasdev)
Your Dear Future Me card is, I’d argue, better than mine:
I hope you still talk to your family every week and that you find what you’re looking for.
The first half is easy. My biweekly calls with my parents — taken usually during my commute — have been replaced with weekly family-wide FaceTimes. Each one has the same tenor: we talk about what we ate, we talk about what we’re watching on television. My mother chides us for not getting enough exercise and sleep; my father asks us about the Dolphins. It is monotony in a time during which I am — we are — so desperate for monotony, for a little tether in the day that we can hold onto, lest the March Thursdays interminably bleed into April Mondays.
The second half is a little bit, erm, murkier. There’s little in my life that I can pin to September of 2018: I am still working at Stripe, and I am still working on Buttondown, and very little else feels similar. People have warned me that as you grow older the years blend together, but it feels like the opposite — the past two years were a foreign country to which I have lost my passport, to butcher a metaphor. To try and remember, I (embarrassingly) consulted my media diary, which is a day-by-day record of all my content:
I was reading Sense and Sensibility and Convenience Store Woman; I was watching Bojack Horseman; I was playing Rocket League. This is perhaps a reductive lens with which to view the past, but it is an effective one, because I remember the other bits too: I was dating someone new for the first time in a very long time, and very nervous (I am no longer dating them, a fact that even then I don’t think I would be surprised by). I was starting to reconnect with some friends from college. I was feeling a little overwhelmed — September was one of the last months that I was freelancing heavily in addition to my work on Buttondown (and, you know, my day job). I lived in a fancy loft apartment that I liked but did not love; I was trying to lose some weight.
Most of those parts of my life, though, have completely vanished:
One anchor, though, is that I am still feeling overwhelmed. It’s hard to tell how much is due to the, as you say, gesturing wildly everywhere of it all, but I don’t think I can use 2020 as an excuse. I’m looking at what’s on my to-do list today, and I don’t think I can in good faith blame its chaos on the coronavirus: Stripe work bleeds into Buttondown work bleeds into cooking and cleaning and reading and writing and all the modern demands we impose upon ourselves. My lists grow longer and longer with each passing day, and each productivity book in which I try to find salvation seems to fail me.
A colleague asked me a few days ago what I would do if money was no object, and it’s been gnawing at me a bit. Yesterday it would be working on Buttondown for ten hours straight; the day before that, it was “the exact same thing I’m doing now.” Today, I think, it would probably be “read for six hours a day.”
And, sure, I think about leaving my job. I think about the time two years ago I told myself “if I ever hit $3,000 MRR, I’m dropping everything and going solo” — and I think about how I moved the goalposts last month to twice that amount.
I think about the work I enjoy; I think about the people with whom I love working, about the things I get to learn and the mission that I do, on the good days, believe in.
(And yes, I think about having to remove a proper noun from my Twitter bio, and the scary parts of independence — what it would mean to leave and to fail.)
But all of this angst is academic. I am writing this from my iPad Pro (on a brand-spanking-new Magic Keyboard, an implement with which I have cleverly reverse-engineered the concept of “having a laptop”) in my backyard. It is seventy four degrees; I have an avocado, a Topo Chico, and a pilsner by my side. My partner is sunbathing, and my bike is resting supine after a thirty mile ride around Lake Washington. It’s difficult for me to worry too much about life: stasis, lately, has felt warm and smelled like fresh linens.
So let me ask you this. How did leaving Peloton work? When — and why — did it feel right?