Do the risky stuff
My immigrant origin story is not the neat “family moves to America, works their butts off, sends their kid to a good school” kind. Mines the messier, grew up poor, moved out at 16, figure it out by making mistakes kind. The details aren’t important, but lets just say I’ve learned the hard way that life is a series of calculated risks.
I don’t do the typical career hoping for a salary thing. I’m ok taking a pay cut if it means I get to work on something challenging, or with people that level me up. I’m not afraid of walking away from some comp for a chance to work with the engineering equivalent of a D1 sports team. Even if I’m just the scorekeeper (self-deprecating ex-o11y engineer joke).
These are calculated risks because im trading short-term comp or “title prestige” for future potential earnings, by broadening my experience and betting it’ll level me up.
I spent a lot of my formative years at Rackspace. The first time I really made this choice semi-consciously was there. I was in support, and I had two options:
- I could go and work on the Rackspace DNS infrastructure team. Interesting work in a established problem space. It paid slightly more than I was making.
- I could go work with a bunch of super smart folks, build this weird thing called NAST to compete with this new S3 thing? Less money though.
On paper, the DNS team was the safer bet. It was the equivalent of job hoping to a new co for more pay. But I took the riskier option. I had no idea what S3 was, but a couple of people I really respected were locked away offsite, hacking away in a dark office, and really excited about building something to compete with it. Sign me the fuck-up!
I’ve never regretted making the leap somewhere, even if it’s for less comp when im betting that the people there are smarter than me and will level me up.
When the writing was on the wall at Rackspace I could have gone somewhere safe in OpenStack land. But instead, I took a stupidly large pay cut (I suck at negotiating) and went to go work at a PE firm for a couple of years. The blip in earnings was worth it. You don’t work for folks like Lew and Paul and not learn something.
16 months ago I took another calculated risk, I went to go hack on a startup for friend - in a domain I knew nothing about - maybe the worst time ever to do a startup since the dotcom bust era? eh, TBD.
My contribution to our best chance of success there was not going to be “build this perfectly scalable architecture”. But “get useful features in front of customers asap” because that would help us find product market fit, and that would let my founder figure out a sales motion as fast as possible. Hard learned lesson from my stints at Scaleworks and Netlify.
We started in Jan, had product in front of customers in like 3mo, completed the SOC2 dance by summer. Our tiny team built a lot of features in a very short time.
Me being able to execute and contribute to that is a direct result of all the calculated risks I’ve taken in my career, because I’ve collected all these experiences, skills, and strategies from those other orgs and the people in them.
It’s easy for me to give this advice while I have a job, in what’s a very sketchy job market for engineers, but:
go take that calculated risk
Swallow your pride and take that lesser job title if it gets you on the bench of a D1 engineering team if thats what it takes. I have, its humbling and worth it.
Ask yourself if that block of vesting options you’re waiting on will really matter in a few years if you’re not growing in your current role. Its probably not, so go take that job with the interesting problem. I’ve done that too, its also worth it.
It’ll be fine. It’ll work out. Probably.