Talking to a candidate the other day who described himself as "being on my second lap", I thought, yeah. That resonates. For me, this is what my career looks like so far after over 20 years in tech:
- Studied Computer Science at SDSU
- Worked as an IC and then later as a Director at a retirement planning brokerage
- Started businesses, cofounded a seed-funded startup, Startup CTO
- Enterprise Principal Engineer, doing architecture and systems designs
- Then back to my true loves: People & startups. Senior EM at a Series A turned Series B healthcare research rocketship
There was a time when my age worried me. Sometime around my mid-30s: Silicon Valley was the hot show, and I was very concerned about aging out and how valuable was a 40-something technologist, anyway?
As turns out: Very much so. Every day I find myself referencing and making decisions from something experienced along the way. Whether it's people management mistakes, making a poor hire, or microservice complexity explosion, having been there, done that gives me the kinds of sniff tests that often lets me smell trouble long before anyone else sees it.
This kind of career path wasn't talked about when I got into industry. Back then the thought was, well, it's one way up the ladder. And if you ever fall off, then you're stuck at the bottom for good. Not the case anymore.
Will I go for a third lap? It's hard to say, but at this point my lean would be why not. I've never lost the deep love for programming and for building that I've had since childhood. Building orgs is fun, and I'd be perfectly happy to keep doing this. And... if an opportunity comes up someday to focus again on writing code? A third lap sounds like a good challenge to me.