Life: What I’m Up To

I’m currently sitting in a comfy overstuffed leather chair in the Rocking Frog in Portland, Oregon. It’s sunny and hot (like 90F) and it’s mid-April, and that’s not what you really expect from Portland in April, but I’ll take it. Seems like a good opportunity to update folks on where I’m at and what I’m up to.

The Catch Up

Most recently, I was running around California and Oregon with my parents, who flew out and visited for the past two weeks (they hopped on a plane back east this morning). It’s been a good (if tiring) visit — my brother and I usually fly back east to see them, so it was nice for them to come out so we could share some of our favorite places out here.

As for how I magically have the time to run around for two weeks: I was let go from Dropbox in late March. While it would have been nice to have a bit more control over my exit, I’m sort of relieved to be out. I’m still bullish on the product and company in the long-view, though it’s a painful and stressful organizational period there right now (we went from 500 to 2000 people in the 2.5 years I was there. If you don’t think that causes growing pains, you’ve either never done it or are deluding yourself). I’d not been getting along with my manager for most of the winter, so it wasn’t really a surprise.

That’s basically the catch-up: I was working a lot, and that wasn’t leaving a lot of energy or headspace for working on my own projects, growing socially/personally, traveling, etc. I did make it out to Death Valley for the super bloom in early March, which was delightful (I may post pictures soon — need to do a little retouching: the perfect time to notice some dust on your camera sensor is right when you get BACK from a trip). If anything that trip just reinforced how much I didn’t want to be where I was any more or doing what I’d been doing.

Now What?

¯\_(ツ)_/¯

The way I see it, I’ve basically got four paths in front of me, and each has benefits and drawbacks.

1. Take another QA gig at another headline company: the benefits are pretty straightforward: they’re most likely to pay the most; it’s a role I already know and do well; and it’s good resume fodder. The drawbacks are arguably just as obvious: I don’t really want to work for another company whose goal is empire; I don’t really want to stay in QA, and I worry if I take another QA job the pigeonholing will be complete; a lot of these high paying “marquee” companies are in areas of the country I don’t really want to live (Bay Area, NYC, LA).
2. Take a role at a smaller company that’s a better personal fit: a smaller company that is doing something I can personally get behind, with a good company culture, in a region I prefer (Portland, Seattle, others?) is arguably worth the potential pay cut, and my breadth of interests is more likely to be seen as an asset rather than a liability. That said, smaller companies that aren’t looking to massively expand hire much more rarely, and take more effort to discover ones that are the right fit, so it may be a bit of a challenge to even find this.
3. Grad School: there’s a program up at University of British Columbia that offers an MLIS with a sub-specialization in HCI (with studies around Human-Information Interaction). I have until June to apply for a winter start, so it’s something I could still actually move on now, rather than needing to wait another year. The program seems like almost exactly like what I’d like to further explore and study, and the HCI sub-focus would put me in good shape for moving into UX and IA after graduating. Also, could be fun to live in another country for a bit. Risks: going into more debt with no assurance of work afterward (VC money is starting to pull back, which suggests two years from now the job market may be much more challenging than now). Also, there’s no assurance I’d get in.
4. Do my own thing: I’ve got a little money saved up (not a ton, but if I move out of the Bay, enough to stretch a reasonable amount of time). My longer term goals have always revolved around having autonomy and pursuing creative projects, so why not try to make that work now instead of constantly putting it off for the “safer” bet? As Jim Carrey commented in a commencement speech he gave, “You can fail at something you don’t want, so you might as well take a chance doing what you love.” This would entail getting back on the writing horse, as well as programming (small, simple, humanist software). This is the most potentially fulfilling option, but also the riskiest.

It’s not like I’m not exploring all my options: I’ve got an in-person interview lined up (of the “go work for another marquee company” type) early next week down in the LA area. But to be honest, I’m leaning most towards the fourth path. I’ve spent so much time cheering others on and encouraging them to follow their passion and dreams — it’s time that I do the same for myself.

One way or another, though, I’m pretty sure I’m done with the Bay area. I’ve given it a fair shake (or tried to at least), and it’s just not my thing. The density of people is too thick, the levels of entitlement too high (NIMBY, FYIGM, and DATM are all alive and well), the gold-rush bullshit hustle too strong, the cliques too established. Also, I miss seasons. I’m going to try and make May my last month where I am (heh, should probably let my apartment know), whether that’s moving for another job, or moving somewhere cheaper while I work on my own stuff (currently thinking Portland: a friend has a room in his house for a reasonable rate, but nothing’s set in stone yet).

If you made it to the bottom of this rambling life update (I hope you like parentheticals!) I’d love to hear your thoughts, whether it’s support, criticism, or advice.