This is the third sending of a penpal newsletter we’re calling Letters to J.
You can read the first or second here
and we hope this brings some needed puttering to Monday’s evening.
(Jasdev ⇒ Justin)
> So let me ask you this. How did leaving Peloton work? When — and why — did it feel right?
Whelp, we’re at letter number three and already asking the last-two-at-a-sleepover-awake-level questions.
I guess that’s what we signed up for, eh?
But, before I get to the when and why, your mention of “March Thursdays interminably bleeding into April Mondays” reminded me of when Thursdays weren’t Mondays and were arguably the best day of the week.
If I’m being honest — and we are — , I felt the first pang of when on September 26th, 2019.
Peloton’s IPO day.
Now, I want to set proper context. I am incredibly privileged and lucky to have been able to leave a job back in March, let alone as a global pandemic upended, well, everything. Getting to a point where I could go independent required managers, teammates, family, friends, and an orchestration of circumstance that I’ll probably never fully realize. It’d be a lie to say it was solo going.
And, in no way does the following reflect poorly on Peloton — my time there was formative in ways 2016 Jasdev was too young to anticipate. I left on good terms and, if I were doing full-time engineering work instead of technical writing, I’d re-apply for a spot on the team.
What was difficult about that day was simultaneously receiving dozens of congratulatory texts while quietly reckoning with fact that I had seemingly followed our industry’s token career narrative (“Join an early-stage company, take them to IPO, [vague hinting at ‘happiness’].”) instead of my own. To be clear, that was never the explicit goal. But, it formed a pseudo vantage point to run towards during my two years across Imgur and Tumblr and then three and a half at Peloton (in the same way the industry almost unilaterally encourages folks to pursue entrepreneurship when it probably isn’t for everyone and that’s okay (!)).
I remember sitting off to the side during that evening’s celebration and feeling so damn lost. I had sprinted towards someone else’s finish line without looking around at what I accomplished along the way. I interviewed and mentored the iOS team from three to nine folks and helped raised the app through its infant years and instead of pausing to cherish that, I kept on running…which, might be cultural conditioning of not “moving forward” as a form of “stagnation.”
The following months were spent wading through a fog of “now what?” And, as most ICs would, I looked to our career ladder for something to climb towards. I was sitting on the senior engineering rung and previously determined management wasn’t my jam, so, I aimed for technical lead. “Now what?” was replaced with “how can I create more senior engineers around me?” I centered on code review, writing documentation, artifacts for future teammates, and gardening a culture where the team could learn without fretting the inevitable missteps (we even renamed “postmortems” to “learning reviews”).
The through line of my tech lead attempt was education. I noticed I’d drop everything — much to JIRA and OmniFocus’ dismay — to help teammates and the larger community with questions around the sharper edges of engineering (FRP, for the nerds).
Couldn’t I stay at Peloton while focusing on education? Sure. Just not at the level I wanted, which was taking a full-time shot at some confluence of engineering education, mathematics, and creative writing.
I found my why.
The when and why met as day-to-day engineering and what I wanted to learn started parting ways. Feature work was fun but it didn’t give me enough time to sit with and write about the theory underlying the architectures we rested on. So, I started thinking things through in probably one too many journal entries and FaceTimes with friends.
The initial plan was touched on in 001 and its current form is:
- write an advanced Combine book; I’m roughly fifty unedited pages in — trying not to self-edit into a corner too early — and am recording videos like this one for certain chapters;
- earmark my days with as much writing and reading as possible.
I think that about covers it, sorry it took — enables word count — 696 words to get here.
Towards shorter word counts, you mentioned a poetry class and an in-progress chapbook when we first hung out in-person. Did it ever come together? And in either case, any pieces from it you’re fond of?
I’d be game to share one of mine in 005.