Vagabond On The Clock: How To Work From Anywhere

Brendan Leonard is the author of The New American Road Trip Mixtape. He lived on the road for almost three years.


Why stay home to “work from home”? Photo by Haris Zlatarevi?

Did you ever have one of those carefree youthful summers to backpack around Europe or live out of your car and do nothing but climb? Yeah, me neither. But through some bad luck and the wonders of technology, I did figure out a way to do something similar while working full-time in my early 30s. Subtract the “carefree,” but add regular paychecks.

A few summers back, I had a five-week sabbatical from my job as a remote copywriter. Just before I was supposed to leave, my girlfriend and I broke up, and our lease ended at our apartment, so I just packed my stuff in my car and decided to drive around and climb with friends until I got sick of it.

At the end of the five weeks, I was due back at work—which in our Brave New World of remote office capabilities meant I just had to appear “online.” I ordered a sandwich and a coffee at Pearl Street Bagels in Jackson Hole, Wyoming, flipped open my laptop and connected to the company’s VPN network. The bagel shop was pretty loud, so I took a 1 p.m. conference call from the front seat of my car, as tourists walked past on the sidewalk.

As I repeated everything back to my co-workers, one of whom was in an office somewhere in New York and another in North Carolina, and confirmed that, yes, I could have the project done by next Friday, I had an epiphany: These people have no idea where I am right now.

I had literally just walked out of the backcountry the day before, after a five-day backpacking trip in the Wind River Range. My last bathing-like experience was in the Titcomb Lakes, the day before that. I had figured I’d go back to Denver after my trip, get a new apartment, and keep working from home. But was that really necessary?


The author hard at work from his “office”

I had my work computer with me, and my phone. My company never mailed me anything. I never had to show up anywhere for meetings. What if I just kept traveling, and used places with public wifi as my new “office”? I was doing that half the day back in Denver anyway—after I got sick of typing at my kitchen table all morning, I’d take my computer down to the neighborhood coffee shop and work from there for the afternoon, just to be around a few other people.

I thought: Maybe I could get away with this, full-time.

The next morning, instead of driving back to Denver to find an apartment, I drove to Seattle to stay on a friend’s couch for a while. I tried out my “anywhere office” idea all around the city—All City Coffee, Zeitgeist, Bauhaus, the Seattle Public Library. During my lunch hour, I would switch “offices.” I found quiet spots for conference calls. If I wanted to go sightseeing or wandering around the city, I did. As long as I worked 40 hours and turned in my assignments on time, no one seemed to care where I was, if I was doing my job.

For the next two and a half years, I worked from everywhere: coffee shops, public libraries, hotel rooms, airports, planes, the occasional McDonald’s, campground picnic tables, laundromats, friends’ kitchens and living rooms, an Amtrak train traveling from Los Angeles to New York, in every Western state, New York, Mexico, Norway, Switzerland and Italy.

From the photos I took with my phone every week on trails and peaks around the West, it might have looked like I was on an endless road trip—but it was far from a vacation. My workdays stretched into evenings, if I decided to climb or go for a mountain bike ride in the morning or afternoon. Americans spend an average of 50 minutes a day commuting, and I spent at least that much time tracking down wifi or moving to the next “office” when I felt I was overstaying my welcome at a coffee shop. My work week spread out over six or seven days—I’d spend half or all of a weekday driving or flying to the next place, and pay for it with a Saturday or Sunday in the office.


And thanks to technology, many people can be; photo by Brendan Leonard

I was able to see the world while still working, graying out the borders between “work,” where we traditionally wear some sort of work uniform and show up at an office during typical daytime hours, and take a few weeks a year to “play,” or take paid vacation and travel somewhere. I probably mountain biked and climbed about the same amount as the average Joe—I just got to do it in a few more places, instead of being limited to the trails near my office or home.

I found people on social media who were doing the same sort of trust-fund-less travel, but with different careers: The folks from Where’s My Office Now, Ryan from DeskToDirtbag, the couple from The RV Project, and other people who volunteered on organic farms throughout Europe to afford to travel the continent on a shoestring. It felt like we were getting away with something, just a little bit. Mostly, I wondered: Why aren’t more people doing this?


Lunch break

At least 10 percent of the U.S. workforce (about 30 million people) works from home at least once a week, and more than 3 million Americans work completely from home. Depending on which statistic you read, most of us are working while we’re not at work anyway—a recent survey found 81 percent of us read our work e-mail on weekends, and 59 percent of us try to keep up with our work e-mail while we’re on vacation.

So why stay home to “work from home”? Can’t we take that conference call in the parking lot of Eddie McStiff’s in Moab and then go ride Porcupine Rim just as easily as doing the call from our home office? Instead of waiting until Friday afternoon to drive out of the city, couldn’t we beat the traffic and head out Thursday night, work a few hours on Friday from a public library and then hit the trail just as everyone in the office enters the “I’m just going to act like I’m working for the last three or four hours of the week” vortex after lunch on Friday?

We’re all working outside of work hours—and outside of office buildings—nowadays, each to our own extent. If you travel for your job, you’ve probably taken business calls in airports (I know some of you have in airport bathrooms), typed e-mails on your phone just before your plane takes off, and opened your laptop in a coffee shop, restaurant, or waiting room to read reports or check spreadsheets.

We used to clock out, loosen our ties, and drive home after work, leaving everything at the office. No one does that anymore, so if you’re taking work with you when you leave, why not take it somewhere interesting?

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