I’ve been doing a review of my life every year around my birthday since 2006. You can last year’s reflection about digging deeper, and the other 12. The primary formative event of my last year was changing careers and re-entering the world of independent creator living.
Large & small
One way to see this is as a cycle I’ve now been through twice of moving from large companies to small companies. This year I oscillated back to independent creative work after 6 years at big tech companies. A brief history of my career is: I joined Amazon in 1998 and left in 2003. From 2003 to 2012 I co-founded several startups (Robot Co-op, McLeod Residence, Habit Labs). Technically Robot Co-op became part of Amazon during that time, but I left before it was re-absorbed into the mothership. From 2012 to 2019 I spent another six years at Twitter, Slack, and (briefly) Patreon.
Green is when I worked at these companies. The y-axis represents approximate number of employees at the company, on a logarithmic scale.
And here I am back on the 1-human rickshaw. Honestly, when I joined Twitter in 2012 I didn’t think I’d last more than a year or two at larger companies, but I think I underestimated how meaningful and creative the work there would be. I’m ready for another year of independent work, but at this point I see the trade-offs at both ends of the pendulum.
It’s tempting to always rationalize why our current position is optimal, but as I get older it’s a lot easier to see how things …