Having a Career Again

For the last five years, since moving to Portland, I’ve been obsessed with building a viable startup.

During that time, I was either working on my own startup as a founder (or cofounder), or working a regular job just long enough to get the money to try again with another startup. None of those four startups made it (one came close). In the process, I established a pattern of not sticking around long at any place I didn’t create.

Now that I’m over the startup founder bug, it’s time to go back to having a career.

Right now I have two problems to solve:

1) What’s the best entry point?

My last pre-startup-obsession jobs were “Senior Software Engineer” and “Engineering Manager”. I also have the skills to be a Software Architect, DevOps Engineer, System Administrator, CTO, Director of Engineering, Project Manger, or Product Manager. But with the exception of CTO, I haven’t done any of them exclusively over the last few years.

So far I’ve been applying to anything that looks interesting – anything I could see myself doing well for a while and enjoying. That list is pretty broad.

2) What place(s) won’t be too concerned with the lack of consistency over the past few years?

I imagine this is probably one of two types of place – one where the person doing the hiring has also been a startup founder, or something that is contract-to-hire.

I don’t really know how HR people think, but I need to find a good way to convey that yes, I did have a disease that causes flakiness, but I’m cured and would like to find something to stick with for a while.

And for the sake of all that is good, please no pre-revenue startups. I’ve eaten enough of that sandwich.

As an INTJ “Mastermind” type, the times when I’ve enjoyed working the most are when I’ve become a broad subject matter expert with an answer to just about any question and the power to create solutions that make user/coworker lives better. That only happens after being somewhere a while and getting to know all of the systems thoroughly. Promotions and raises are pretty enjoyable too.

I’m not sure where I’ll end up next, but finding the next thing is probably just a numbers game.