I left my newspaper job in 2007, in part because I wanted to go on a three-week trip.
There was no way to accommodate my being out of the office that long — working remotely was so completely out of the question that the possibility was never even mentioned — so I gave my notice, and the paper lost a valued (I think!) employee.
This year, when I told my boss I was thinking about going to Europe for the summer, his response was something to the effect of “oh, cool. Have fun.”
When you’re already an offsite employee (my house is about 1,000 miles from the Chicago office), for a company that extols the benefits of a remote team, it doesn’t much matter where you’re working from. I took advantage of that flexibility and spent my summer working from Scotland, England, France, and Ireland.
For 37signals, the main advantage of a remote workforce is the ability to attract and hire the best people, no matter where they live. But for me, remote work is a major employment benefit. More than a 401k, more than a health care plan — the fact I no longer have to save up vacation time to take one or two short trips a year is huge. I don’t have to wait until someone gets married or dies before I can go see my family — I can just go see them, and work while I’m there. If my girlfriends are going to Mexico for a week but we’re slammed in customer support, I don’t have to choose between letting down my pals or letting down my team. Gone are the days of spending precious PTO on obligatory holiday travel, resenting how I’ve still never seen Vietnam.
I mostly stayed with AirBnB hosts, anywhere from a few days to a few weeks at a time. Since all I need for my work is my computer and a reliable Internet connection, I just made sure before I booked each place that I’d be able to get online.
Sure, there were snags. If I did it again, I’d want to be more on top of the schedule, more available by phone, and more certain of an always-reliable Internet connection. I felt guilty toward my team and our customers whenever issues along those lines arose. My next computer will likely be an Air — the MacBook Pro is great, but probably packs more oomph than I need, and it’s a bit of a beast to lug around. And I’ll likely be more mentally prepared to work different hours from the rest of my team. Euro hours are quieter and I could get a lot done, but they’re also kind of lonely when you’re used to hanging out in Campfire with your work buddies all day. Of course, now that we’ve hired a few folks overseas, that may be a moot point.
Overall, though, I found my work was highly portable. I could always get what I needed, and my team and my company were super-supportive. I had an amazing time, and felt beyond lucky to work for a company that lets me — encourages me, even — to live a life like this.