On to my next adventure

It seems like forever ago that I took on my first team at TripAdvisor – I was working with two junior engineers (both of whom had more experience with the codebase than I did), some tools and forum code, just muddling my way through. Almost five years later and I’m responsible for six teams, with almost 40 people working on code I’ve never touched, still somehow muddling my way through.

The more people you manage, the more teams you’re responsible for, the more difficult it is to have a significant effect on any one. When you don’t know the codebase, it’s way more difficult to understand if time estimates are reasonable, if architectural decisions make sense, or really to provide any kind of technical oversight. And on some level this is OK – at this point your job is mostly to build strong teams with strong leads you can trust, make sure the right questions are being asked (and mentor your leads to ask them), help to remove bottlenecks without becoming one yourself, be the adult in the room during crises, and just generally to help everyone get along.

This is all true. Unfortunately, it’s also true that there’s an unscratchable itch that’s been getting progressively more urgent over the past couple of years. Dress for the job you want, they say, and I have to admit – I used to dress in button down shirts, jeans, and nice shoes. Somewhere along the line I switched almost exclusively to hoodies. I wrote blog posts like this (and this, and this), and almost had myself convinced that I could be satisfied coding at home, or doing the odd script. But the itch never went away.

So, the time has finally come to take my own advice, and to make a non-linear change. I’ve been climbing the ladder for a while – taking on more and more responsibility – but it’s time to turn to the left, go down a flight of stairs, and explore something new. Time for a new adventure.

I’ve done a lot of recruiting at TripAdvisor, and the most common question I get is, “why do you like working here?” I generally talk about the people – how we have an extremely strong technical team made up of really nice people, how it’s a very supportive environment, how we don’t have brilliant jerks (it’s just not that kind of place), and so on. Then I talk about how the work is really interesting, that there are hard problems to solve, it’s fast-paced, no red tape, etc. But there’s one more thing that I’ll be adding to the list, and that’s the flexibility to explore different roles within the organization. Whether it’s hacker weeks, inter-team swaps, or the engineering rotation program, it’s in our DNA to provide different opportunities and to encourage people to try new things.

And so, starting in a couple weeks, I’ll be joining the TripAdvisor operations team as an individual contributor. I’ll be drinking from the firehose for a while – sure, I’ve administered a couple of servers for my own website, but never anything even remotely at this scale. It’s probably the scariest technical job I can imagine, which is how I know I’m making the right choice (or doing something incredibly stupid) (or both) (probably both) (holy crap I’m an idiot). Time to start working on a neckbeard.

I’m sure I’ll end up managing again at some point, but for now I’m looking forward to the incredible luxury of being able to focus on a single set of responsibilities, along with a massive reduction in time spent in meetings. In the meantime, while I’m sure I’ll still have things to say about management, I’m also hoping to be able to share some insights on operations gleaned along the way. Watch this space!

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