Become a Digital Nomad: Get Paid While You Travel the World

Nine-to-five desk jobs are so passé. Become a digital nomad instead and adventure while you work.

WORDS Words Hannah Stuart-Leach
April 2018

Illustrations Maily Degnan

Have laptop, will travel

American culture has long had a soft spot for the drifter—the restless, lonesome Kerouac type with a rebellious streak and a flexible approach to personal hygiene. Today, that impulse to wander away from the tribe has been sanitized, monetized and repackaged as a group activity they call “co-living.” The trend is centered on repurposed homes around the world—owned and operated by outfits like Outsite, Roam and Common—in which “digital nomads” share living and work spaces in an effort to shed the bonds of a dreary 9-to-5 existence. In fact, it’s entirely possible nowadays to crunch your company’s marketing budget from the confines of a Tibetan yurt—if, that is, the yurt in question has Wi-Fi.

If you’re under the age of 25, you’re most likely rolling your eyes in a no-duh way right now. But if, like me, you’re in your 30s or upwards, co-living can come across as one of those trends—like Instagram shopping and face filters—aimed exclusively at the #HerschelBackpack generation.

Yet I was intrigued. What would it be like to dip into this world, and would I want to stay there? I did some research and found that many of these co-living accommodations are far from the dorm-like, who-ate-my-Pop-Tart dives that haunt every college grad’s memories. Indeed, Outsite promises to provide its clients with upscale spaces “in beautiful places.” A resident of Bristol, England, I’d always longed to visit New York City, so I checked out a property of theirs in Brooklyn, which did indeed look very nice. I browsed the testimonials, too, which were littered with phrases like “amazing towels” and “great food.”

Sold to the lady without a Snapchat account!

Home away from home

“Sorry, what exactly are you doing again, darling?” my mom asked when I told her about my plans to become a digital nomad. Midway through my explanation, she butted in: “Did I tell you the dog got a new haircut?” Even my relatively clued-in boyfriend, Tom, persisted in referring to the trip as a “holiday,” despite my increasingly shout-y claims to the contrary.

Actually, I understood the confusion. There’s something disconcertingly neither-nor about this co-living thing. I wasn’t going on holiday, but I wasn’t moving either. I’d be away for a total of two months, but during this time I’d be living a new life, shared with new people—like a season of Big Brother where the housemates have to earn a living. Maybe I’d end up getting evicted. I really didn’t know what to expect.

My arrival in New York coincided with the end of the city’s famous marathon, and I couldn’t help but feel a sense of solidarity with the runners I saw hobbling through the subway, shivering proudly under foil blankets. Unlike them, I hadn’t just completed a 26.2-mile run, but I did have a large wheelie case with me, and many stairs to navigate. We were all in it together, I thought as I watched a rat foraging on the tracks, finding our way through subterranean Gotham in significant shared discomfort.

I emerged from the Grand Street station into a cold, clear night, which didn’t quite tally with the perspiration gathered on the forehead of the red-faced fellow who greeted me outside. I was a bit surprised to find that this particular part of Williamsburg was still under construction, but figured it must be the “edginess” I’d heard so much about. I discreetly consulted my phone, then pointed myself in the direction of the Outsite apartment, located in one of the area’s dimly lit former warehouses. A few fraught minutes later, I found the property, climbed the stairs and—at last!—entered the co-living scene.

Well, I say scene. The lights were off when I arrived. My new roomies, it seemed, were enjoying an early night (millennials, huh?). So I headed straight for my room, aspirationally named Park Slope, which flickered with the lights of a police car parked outside. I fell asleep (eventually) in a bed that reverberated slightly to the beat of what I presumed to be trap music. I couldn’t have been happier.

Office relationships

The next morning, eager to check out my new digs in daylight, I prepared to venture out of my room. Co-living spaces vary in style, from hostel-like properties where you get your own bunk bed to more luxurious homes where you’re granted your own en-suite. The duration of each stay varies, too, from a few days to several months. And, of course, the longer you stay, the more important it is that you get along with your fellow nomads.

I’d judged by a quick door count the night before that I potentially had nine roommates to meet, which was a little troubling. Although Outsite assures guests that their housemates have been vetted beforehand via online questionnaires (Are you, or have you ever been, a sociopath?), the fact remained that I was about to enter a domestic relationship with a bunch of people I’d never met.

The first concern was: What am I supposed to wear? I wasn’t dressing for an office, but I didn’t want to walk around in my PJs. Or did I? I dashed on a bit of mascara and even brushed my hair, then padded into the communal area in sweatpants and socks, a terrible grin fixed to my face, and met … nobody. Everyone was still in bed.

Thankfully, the place was just as nice as it had appeared on the website, all white space and clean lines, with a monochrome kitchen, bare bulbs and exposed brick walls. I made myself a coffee, opened my laptop and set about the business of staring blankly at the screen. Every now and then, a distracted-looking 20-something would shuffle in and join me at the table. There was a superbly dressed couple from Ireland, a wine buyer from California and a German guy who did something corporate for IBM. I was buzzed-up on caffeine and keen to chat, but quickly got the sense I should save it for later. This was work time.

Once I got into the groove, I rattled through my assignments with ease. The apartment had all of the benefits of working from home, without the time-sapping temptations. (It’s hard to ease into a Gilmore Girls marathon when you’re sharing a desk with a load of dedicated “disruptors.”) And the Wi-Fi—oh, the Wi-Fi! This signal was so strong you could practically smell it. Yes, there was the odd knuckle crack from across the table, the occasional overly emphatic sniffle, but I could tolerate almost anything for dependable Dropbox.

Later, when I popped out for lunch, I noticed an agitated young woman trying to work in the cramped corner of a chic-looking café—cool on Instagram, no doubt, but limited to the size of a closet by the city’s extortionate rents. How many unwanted flat whites would she buy to justify staying there? With a spring in my step and an everything bagel in my pocket, I skipped back to the apartment, where I belonged.

The cast of friends

If you can’t stand the question, “So what do you do?” co-living is not for you. Networking is part of the deal here, to the extent that you’re obliged to write down your name and profession on a chalkboard. Eager to fit in, I’d added mine to the list of developers and designers in a jaunty pink cursive. People asked anyway.

But the relationships forged during these trips often move beyond the professional. Sure, the initial bonds arise from the fact that you’re all grappling with the logistical enigmas that arise from working really remotely (“So when you say you need this by 12, is that noon GMT, midnight EST or Thursday CST?”). And out of this shared experience, there arises the tantalizing possibility of genuine and lasting rapport—a prospect that is eagerly fed by all of the co-living companies.

Like most properties run by Outsite (motto: “Stay, Work, Play”) the Brooklyn apartment was designed to make it easy to meet and mingle, hence the open-plan setup, which everyone had to walk through to get anywhere. There was even a rooftop hangout, where bonds could be forged beside an artfully corroded vintage bike. As the company website puts it: “Our members keep in touch, share travel adventures and are always ready to learn more from each other.”

It was the responsibility of the house community manager—a charismatic New Yorker named Arielle—to foster these budding friendships through a succession of potlucks, parties and group excursions. I’d actually managed to corner a few housemates on my own, thanks to the kitchen-side location of my room. As soon as I heard the click of the kettle, I was out the door, casually gasping for refreshment. One evening, I bonded over a mint tea with Robin from Berlin. We got on really well, largely due to our shared passion for Christmas. Then, just as I thought we were about to exchange numbers, Robin excused himself. “Right, I better get an early night. I’m leaving tomorrow,” and just like that I was on my own again.

My spirits rose the following day, when I received a group email from Arielle inviting us to a bowling night. Woo-hoo! Actually, I’m not a big fan of bowling. It brings back memories of the insurance company I did data entry for as a student, and the enforced after-work socializing that sometimes entailed. But on this occasion, I not only replied to Arielle’s email invite within seconds, but was the first to ‘like’ the Facebook invitation. A bit embarrassing, yes, but here, at last, was a chance to forge relationships with people who, up to now, were distinguishable mainly by the relative ferocity of their keyboard tapping.

Unfortunately, my fellow nomads apparently liked bowling even less than I do, as the bonding session that night amounted to Arielle, a cheerful marathon runner from Boston named Xiao, an Australian physiotherapist called Stephen and me. Thankfully, we ditched the bowling idea and had a nice dinner instead. Over a plate of chicken wings, Stephen, a bit older than me, revealed he’d come here on the advice of his meditation teacher in Sydney.

I’m not sure what I expected the typical nomad to be like, but neither Xiao nor Stephen were it—and I was delighted. I loved being thrown together with these random people, exchanging life stories and New York survival tips (“So, if I get a takeout single-origin latte with no pumpkin spice or foam art, do I tip?”). It was all the interesting bits of speed dating without the awkward prospect of romance (although that happens, too, I’ve heard). Or, to look at it another way, you bypass all the giddy flirtations and go straight to sleeping in separate rooms.

Like a local

Work actually turned out to be a secondary aspect of the co-living experience for me, partly because it was so easily taken care of, and partly because, well, it’s a lot more fun making friends than meeting deadlines. I was relieved to find that my age wasn’t an issue, probably because, over time, we all understood that we were sharing a good deal more than dishwasher duties. The feeling of community, meanwhile, gave me a sense—far more than the confines of a hotel room or even an Airbnb—of being at home, as did the simple act of having to go to work each day. After one short week in New York, I’d almost started to feel like a local. I’d found myself a yoga studio, dive bar and pizza joint—and was convinced all three should be combined in an immersive pop-up.

When I did explore the city, I tended to do things that had been suggested by people rather than guidebooks—my favorite adventure was a candlelit cacao ceremony with some hipster witches who helped me channel my animal spirit. (I’m a lizard, apparently.) Back at the apartment, I no longer tiptoed around my housemates. Instead, we lounged about on sofas talking nonsense, like you do. One particularly spirited discussion revolved around the culinary value of tacos, which I had described, controversially, as “less-filling burritos.” The only real disappointment, in the end, was discovering that Central Perk is not a real café.

My stay in Brooklyn ended as it had begun: with everybody in bed. I had an early flight to catch, so I left a goodbye note which may have been slightly over the top. I felt sad to be leaving and grateful for the experience, which led me to compose an extended prose poem about gratitude and sorrow. I left my email address at the bottom of the note—along with a heartfelt plea to “Keep in touch!”—but no one has written yet. I’m still hopeful that someone will drop me a line, but I wonder, too, if a Snapchat handle wouldn’t have been more effective.


More Business

Zenni's Hindsight Is 20/20

Sights set on Summer

These Businesses Are a Family Affair

This Singapore shop only carries products created through crowdfunding