Leaving Automattic

Yesterday was my last day at Automattic.

Leaving a remote job is a little unusual. When I checked out on the last day, I was sitting at home. I said goodbye to my colleagues online, and closed Slack. It was otherwise the same as any other Friday. There was no office to leave, no boxes to pack, nobody to hug, no hands to shake. The first sign that my employment was properly ended was an authentication error from the proxy server.

Fortunately, I had a chance to say goodbye to my team and a few others in person a few weeks earlier. Even after I gave notice, Automattic was generous enough to keep my booking to the team meetup in Portugal. It was great to have the opportunity to say goodbye and spend some time with colleagues (many who I hadn’t even met in person) before signing out a few weeks later.

Automattic was such a fascinating place to work. If you’re interested in the inner workings, I highly recommend The Year Without Pants by Scott Berkun from his tenure at the company several years ago. It’s a pioneering company in so many ways - remote work, open source, HR, team structure, all are nonconventional in some way. Of course, like any company it has its challenges, but the way that these challenges are faced and dealt with is something I could never imagine in most companies of its size (600 and counting). Chats with HR are actually enjoyable, decisions are made based on facts more than politics, and everybody is incredibly switched on, interesting, and motivated. The hiring bar is high - it’s a long process including a trial period, so to get in you need to be good at your job rather than know somebody senior. I’ve made some amazing friends there, and had the opportunity to contribute to some really interesting (and open-source) projects.

With that said, it might be obvious from the above that it was a really tough decision to leave, honestly I think I’m insane to give up such a great gig. But I had ideas brewing, and once you get that itch it’s hard to avoid scratching it. The best part of leaving a remote company is that I’m no further from my colleagues and friends than before. We’re all still using the same internet, even if we no longer interact every day.

What's next

I've decided to take some time to work on project ideas I've had brewing. I've added to a growing list of ideas over the years, and now I'm really keen to get started on some of them. I couldn't build these while working a full-time job, both because it's exhausting to use spare time to work and because Automattic isn't so keen on moonlighting. So, I decided to rip the bandaid off and dive right in. I have some savings to survive on - by living extremely frugally I think I can stretch it to almost a year without income, and I plan to pick up a few freelance gigs along the way. Next week I'm moving house; once that's out of the way I'll let you know the details on the master plan :)