At my previous job I would get antsy sitting in the same desk every day. I would move around a lot. I’d find an empty desk, an unused conference room, or sit at the picnic table outside. Although I was moving around, it was hard being creative sitting in the same general location and feeling like you had to more or less be physically present from 9–5.

One thing I’ve come to appreciate at my gig here at Automattic is the ability to completely choose your own adventure in terms of when and where you’d like to do your work. I’ve been here less than two years and my list of “where” is pretty long and continues to grow.

I used to take a lot of working vacations, but I’m learning that just because I can work anywhere, doesn’t mean I should. Working on the beach may look cool in pictures, but unplugging and enjoying your vacation has proved to be much more beneficial. I still believe that working while traveling is a great way to spend time in a new place, but I’m trying not to let all my vacations become working ones.

Lived:

• Ellington, CT
• New York, NY
• Brooklyn, NY
• Monterey, MA
• Moving to Chicago, IL next month

Worked:

• San Francisco, CA*
• Santa Cruz, CA*
• Various towns in CT
• Las Vegas, NV*
• Reykjavik, Iceland*
• Jackson Hole, WY
• Moab, UT
• Denver, Boulder, and Aspen, CO
• Queenstown, New Zealand*
• Various towns on the island of Oahu, Hawaii*
• Salt Lake City, UT*
• Charlestown, RI
• Provincetown, MA
• Seattle, WA*
• Paris, France*
• Boston, MA*
• Atlanta, GA*
• Portland, OR*
• Chicago, IL*

My favorite place to work? Anywhere with my coworkers on any one of our meetups. (Those locations are marked with a *)

Working whenever I want is also important to me. I’m not always the most creative or productive during the “normal” 9–5 business day. This doesn’t mean that I haven’t created a routine, its just a very flexible routine that I’ve iterated on over time. It allows me to not feel guilty getting up from my computer and going on a bike ride at 2pm three days in a row and gives me the ability to say “yes” to an impromptu long weekend.

If any of this sounds interesting and you’d like to come work with me, check out our job openings. I know remote working isn’t for everyone so if you’d rather work in an office with a great group of people, my previous company is hiring as well.

Photo: Taken in Boston, MA by coworker Jeff Golenski