Gone Fishin’

At the end of the day, I’ll begin a sabbatical from Automattic that will last until October. It will be the first time since 2004 that I’ve had more than two consecutive weeks away from work. The idea of not working for an extended period of time is all at once exciting, relieving, and terrifying. But I’m grateful to work for a company like Automattic that not only allows but encourages employees to take time off when they need it. As I take this break, it seemed like a good time to reflect on how I got here.

In the summer of 2005, Matt Mullenweg got in touch with me to do some freelance design work1. He was starting a new service called Akismet, and I built a very simple website to introduce it to the world. We worked well together, and a while later he asked me to design the logo and website for a new company he was starting called Automattic. It was the biggest project of my very short career, and was soon followed by a bigger one: the redesign of WordPress.org that launched in December 2005. In the middle of all that, Matt asked me to join Automattic full-time. And I said no.

It wasn’t that I was skeptical of Automattic’s prospects. But commitments are important to me. When Matt made the offer, I was just three months into my first real design job. The company had taken a chance on me, a self-taught web designer with a degree in print design, and had helped me move to Baltimore for the job. I told Matt that out of loyalty, I wanted to stay there for a year. But in my spare time, I continued to freelance for Automattic. And after that year was up, I decided to join full time. Yet after almost seven years, Matt still likes to introduce me to people by saying that I rejected him the first time he offered me a job. :)

My career at Automattic has been the most fun I could ever imagine having while working this hard. It’s been thrilling to help both Automattic and WordPress grow from their tiny beginnings. And I am nowhere close to done. The last survey taken by A List Apart shows that over half of the web professionals surveyed had been in their job two years or less. Just over 10% had been at the same company for seven years or longer. And no knock against designers who changes jobs more often, whether out of necessity or choice. But I’m inspired by designers like Dieter Rams and Jony Ive, professionals who built careers designing products largely for a single company. It’s certainly possible for a great designer to do good work for many different clients, without spending much time with any one of them. But I’ve never considered myself to be a great designer. I’m a designer who’s determined to produce good work, and I have to work hard at it. Creativity and inspiration do not flow through me like a typically “artistic” person. But I love design, I love the things I work on, and nothing excites me more than seeing that through for the long term.

So no, I’m not leaving Automattic. I’m planning to spend some time both relaxing and working to accomplish some personal goals I’ve been neglecting for too long. I plan on spending a little less time in front of my Mac. I hope to find a new place to call home. But most of all I’m looking forward to coming back to Automattic in the Fall with a renewed focus and energy for the work I love.


1 The TextDrive VC200 started my career. When I began teaching myself the basics of web development, I chose TextPattern to power my first blog. I signed up for the VC200, became involved in the TextDrive user community, and did some freelance work for them. Matt Mullenweg asked Jason Hoffman to recommend a designer, and the rest, as they say, is history.

14 thoughts on “Gone Fishin’

  1. I remember you from the TextDrive VC200 days (I’m #141). Doesn’t seem that long ago. :) Everyone needs to take time for themselves – to refresh, renew, chill, whatever the need is at the moment. I’m glad you’re able to take the time you need. Enjoy the rest of the summer, and we’ll see you in September. :D

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    1. Thanks! I’ve forgotten my VC200 number, but it did turn out to be a great investment even as broke as I was at the time. :) Who knows where I’d have ended up if I’d just bought some generic hosting somewhere else!

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    2. I was lucky to meet Matt virtually back then, too (I’m VC #20). I asked Matt to design a logo for me, and what he designed has been at the top of mistersugar.com ever since. (I actually need to ask Matt what font the mistersugar is in.)

      Matt, thanks for taking a chance on me back then, and thanks for being such an authentic person. You should be damn proud of what you’ve accomplished and who you are. Enjoy the sabbatical. If you come through North Carolina, give me a call and we’ll get dinner.

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      1. Thank you, Anton both for the kind words and the invitation! Designing Mr. Sugar was a lot of fun, and one of my first freelance jobs ever. I’m glad to know it’s kept working for you so long! The typeface is Clarendon, one of my all-time favorites.

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  2. In related news, I’m going to be taking over MP6 development!

    …wait, why has my SVN account suddenly stopped working?

    :-D Have fun taking time away!

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