It’s that time, and with the enforced downtime that is the children’s end-of-year vacation, I’ve been taking some time to reflect on all the changes of the past 12 months (and, you know, actually start writing again). Settling into our new home, the children getting older, our daughter finally starting to grow some hair (we make baldies), and of course leaving TripAdvisor for Scratch.
What it was like to leave
I moved to Scratch in mid-May of 2015. At first, there was a sense of freedom. All the responsibilities, the crushing flood of email, ongoing projects, meetings, politics, and worries – all gone. Every ball I was juggling, every expectation, every long-term plan, past success and failure – all in the past. After so much time, I’d taken on a lot of small responsibilities – watching for a particular class of errors, following up on build breakages, keeping an error report (relatively) clean – each a small piece of a cognitive load I hadn’t noticed until it was suddenly lifted.
Free! Well, for a weekend, at least. Then thrown from my comfortable routine into an alien landscape with new people, unfamiliar responsibilities, a different culture, new technologies, processes, tools, projects, and goals. From a place where I’d paid my dues and knew how to get things done (and which things needed doing), to a new team where past successes counted for little, and everything needed to get done, all at once. Furthermore, while a lot of what I’d learned at Trip carried over, some early blunders resulted from trying to apply TripAdvisor conventional wisdom to a twelve person startup.
Probably the most unexpected thing about leaving was feeling like I’d lost a piece of my memory. I’m serious about this. I had years of old email, documentation, a hiring database with comments on thousands of candidates, convenience scripts, aliases, sample code, browser bookmarks, .bash_history files, and a network of experts to consult with on any question – all gone, in the blink of an eye. I’d go to do a routine task – something I’d done a hundred times – and suddenly realize that I’d forgotten the precise sequence of steps, or never really known them – and I couldn’t just log in to server X to trivially look up the answer. It was incredibly… disconcerting… and learning each thing again – for real – was an initially frustrating, but ultimately critical learning experience.
I missed my friends. But I also discovered that there’s a fairly large community of ex-Tripsters in town, and I started organizing lunches and after-hours drinks. All of us left Trip for reasons, of course, but there’s a lot of positive feeling and nostalgia toward the mothership. It’s been fun re-introducing myself to these old friends.
Why I chose Scratch
This has been one of the most common questions friends (and interviewees) ask. Switching jobs can be traumatic, for all the reasons listed above and more, and it was important to me to land in a place where I’d be happy, and where my energy would go toward fighting the right kinds of battles. I briefly considered some of the big name-brand companies, but just didn’t think that I’d be able to go through the same kind of growth curve – or have anywhere near the same kind of impact – at a massive company like Google or Amazon. On the other hand, I’d worked at places with toxic cultures, rampant deathmarches, and where the CEO drove the crazy train up and down wild emotional rollercoasters of hope and despair. Seriously, my number one requirement was to be working with adults, and as much as possible to avoid the cray-cray. I didn’t want to be working in a David Lynch movie.
I also wanted to be doing something good. Now, TripAdvisor wasn’t curing cancer, but they were helping people enjoy their lives more. WordChamp was trying to help students learn foreign languages. Even my time in the video game industry was a means to an end. I didn’t need to be saving the world, but I wanted at least to be leaving it a little better. While personal shopping isn’t something I would have gravitated toward naturally, having just moved into a new house and seen my wife’s and my precious free time devoured by the need to research and buy stuff, Scratch’s mission resonated strongly, and I was energized by the idea of helping others reclaim their free time.
I wanted to work with a great, diverse team, and to learn from the people around me. If we failed, I wanted it to be because doing something new is hard, not because we made foolish, easily avoidable mistakes. I was highly impressed with the people I met, and felt confident that they would be tenacious, capable, and sane.
What it’s like now
Not gonna lie – the past eight months have been pretty tough. In that time the company doubled in size, and the engineering team – four including me when I joined – lost two of its early members, but simultaneously grew to its current six members. It’s hard to overstate how awesome it is to be working with a strong, technically diverse, collaborative, easygoing team. Most successful companies have a core technical team that’s been there from the early days, been through the lean years and the oh shit moments, somehow pulled through and made it all happen. This will be a great base to form the nucleus of our future organization.
I like to joke that everything that was easy at TripAdvisor is hard now, and that everything that was hard there is easy. But I’m no longer a stranger in a strange land, and much of the accidental complexity that made things especially difficult in the beginning has been resolved. When I left Trip, I told my boss that I was looking for my next S-curve – I should have used the plural. The somewhat clichéd fish out of water first act is over, has been for a while, but there are many, many more challenges to come.