2021 Blog Redux (or Why I Quit My Job Twice in One Year)

A rock garden at Byodo-in Temple, Hawaii
The rock garden at Byodo-in Temple (Hawaii)

In January 2020, my wife and I quit our jobs to travel around the world. The flights and Airbnbs were booked. We were all set to leave at the beginning of March, until… COVID-19 had other plans for us. (Our cats were pleased.) After a few months of misplaced optimism, we went back to work, without our planned “travel catch-up” and without my post-startup cleanse.

Cut to 11 months later: I’m still burnt out, only 100x more so. So I made the decision to join the “YOLO Economy” (said The New York Times, not me) and quit my well-paying, fairly comfortable job (again), and go rogue. I re-did my office. I set up an LLC and a business bank account. I uh… bought a domain and resurrected my Medium account for a blog. Now what?

I’m building. At first, it’ll mostly be on my own, but in time, I’d like to start working on “bigger ideas” with friends slash potential co-founders again.

In typical Amazon fashion, I’ve created some tenets for this go-round:

  1. I don’t need to build a billion dollar business. It doesn’t have to be “venture backable”. It just needs to make some sort of profit (MRR > Heroku costs, basically). I’ll work out the details once it’s making money.
  2. It’s OK to build things that fail. At best, I’ve written new code that will be easy to copy for another product idea. At worst, I learned why that idea failed so I can work to learn and iterate earlier, or avoid it, next time.
  3. Build in public. I’ll be blogging (maybe tweeting) and doing whatever I can to share what I’m building as I’m building it. This will hold me accountable and make the products that I’m working on even better.
  4. Lastly, I’m going to go record shopping during the week if I want to! I’ve always kept a rigid work schedule, even when leading Casamatic. If I can take an evening meeting or “catch up” on a weekend, I should be doing the same for things that aren’t work-related during “working hours”.

So, from now until the world opens back up for round-the-world travel, I’ll be here building. And probably during. And almost certainly afterward. And while I don’t know exactly when that travel can happen (probs not until sometime in 2022), I’m really looking forward to just building.

I’m starting by finishing up a side project that I was building for myself, but challenged myself to build it so others could enjoy it too. It’s called Filmstock — it’s a film camera and stock search app and price tracker. It was my first time building something with user auth and subscriptions (and it is so cool to see people using and paying for something I’ve made). And I have a couple other projects already queued up to start next.

2020 bested me, as it did many others. But 2021 is the road to recovery, and it’s hard to ignore the sound of good to come this time next year.

Listen to “This Time Next Year” (The Movielife) on Spotify or Apple Music.




A “product person” working on something new. Ex-Amazon, Indeed. Coffee enthusiast.

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Alex Bowman

Alex Bowman

A “product person” working on something new. Ex-Amazon, Indeed. Coffee enthusiast.

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