Now Working From Home Can Be Working While Seeing the World

"Digital Nomads"—and the startups that cater to them—are changing the idea of "working remotely."
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Surf Office, Santa Cruz.Surf Office

Around midnight on a recent weeknight in Boracay, an island in the Philippines consistently rated one of the most desirable beach destinations in the world, Jay Meistrich is tracking invoices from his hotel room.

Meistrich, the founder of to-do-list startup Moo.do, says he only intended to be in Boracay for a few days while he focused on work—he’s in a “big crunch” right now, clocking 70-hour weeks. But then friends he’d met in Thailand posted photos of Manilla to Instagram and he remembered they’d made plans to meet up.

“I was like, ‘Oh! This is still happening’” says the entrepreneur, who tends to plan his life two or three days in advance. Meistrich extended his stay, and he and his friends—two Norwegians and a Canadian—co-worked from paradise for a few days. Their professions, in this case as a contract developer, the proprietor of a travel startup, and a Chinese translator, are similar to Meistrich’s in that they can be held down from pretty much anywhere, as long as you have a decent Wi-Fi connection and a willingness to Skype at odd hours.

Meistrich has been traveling uninterrupted for just over two years, managing his company from places like Bali, Shanghai, and Croatia. He’s one of the notable proponents of so-called digital nomadism, a relatively new term used to describe knowledge workers who have taken the tech economy’s move away from traditional office culture—and its flexing of the boundaries between work and leisure—to an extreme conclusion.

According to an analysis of census data from Global Workplace Analytics, 50 percent of the American workforce holds a job that could support at least some sort of telecommuting. That number is likely much higher in the tech industry, where allowing employees to work remotely for long stretches of time is “definitely a trend, [particularly] among younger companies,” says Alexey Komissarouk, an engineer who has been on the road for over a year. “For a lot of nomads I’ve spoken with,” he says, “location independence is a perk of their profession, like free lunch or a gym membership.”

Komissarouk co-founded Hacker Paradise, a program that runs along the more mediated end of the digital nomad experience. His company partners with local co-working spaces in places like Taipei or Tokyo and takes remote workers on jaunts for weeks at a time. The vibe at Hacker Paradise is something between an incubator and an intentional community; along with surfing and exploring, participants check in with each other and demo projects. “It’s like—‘I’m in this country where people don’t know what I do, or I haven’t found people who know what I do,’” says Komissarouk. Traveling with a group of like-minded remote workers is helpful so people “don’t feel alienated.”

In the last year, a number of meet-ups and at least one conference for digital nomads have been organized in hip, culturally relevant global cities like Berlin and Chiang Mai. Pieter Levels likely has something to do with the term’s increasing visibility. Levels, a Dutch website developer, worked his way across the world for two years before launching a series of websites catering to the interests of traveling professionals whose status wavers somewhere between resident and visitor. They include Nomad List, a resource that ranks destinations in terms of their cost-of-living, weather, and internet speed, and a subscription Slack channel where members ask for cafe recommendations and arrange to cross paths.

In Berlin—a city once termed the “post-tourist” capital of Europe for its influx of hybrid travelers staying in town longer and seeking more authentic local experiences—the term is trendy enough that a trio of colleagues with ties to the city’s freelancing and co-working scenes launched a survey on the subject this past summer. As they pointed out, it’s hard to tell without a comprehensive study how many self-identified digital nomads are full-timers and how many are on extended vacation writing personal travel blogs.

At its most expansive, digital nomadism could apply to bootstrapping entrepreneurs like Meistrich, professionals taking off for an extended period of time with programs like Remote Year as they log virtual office hours, and freelancers hopping between international co-working spaces and renting Airbnbs. “There’s a big cultural difference,” says Meistrich, among the kinds of remote workers he sees in different countries, much of it dependent on how far the dollar goes. “In Europe, it’s high-end consultants and freelancers, and then when I was in Chiang-Mai, it was people who were trying to start a drop-ship company.”

Depending on their preference, says Amy Truong, a software tester for GitHub who has been traveling for about a year, full-time remote workers may stay in a city for two weeks or a few months before moving on. She’s currently working from SunDesk, an airy house near the beach in Taghzout, Morocco, that shouts out digital nomadism in its website copy. The second-floor co-working space has all the trappings of a startup office: coffee, snacks, and white boards, along with an ocean view.

Some location-independent workers, Truong says, may stay in Airbnbs. But if money’s tight, a few will band together and rent apartments in local neighborhoods, which she likens to San Francisco’s startup houses. For champions of this lifestyle, near-constant traveling is a way to stay fresh in an industry that often requires workers to spend 12 hours a day parked in front of a laptop. “It’s nice to be able to focus on your business and then over the weekend explore a new place,” says Truong, who is also a moderator for the nomads chat room. Plus, as Meistrich is fond of pointing out, he spends less money traveling—including airfare and hotel costs—than he would on rent alone in post-boom San Francisco.

Amanda Klekowski von Koppenfels, a lecturer on migration and politics at the University of Kent, has estimated there could be as many as 7 million Americans living abroad, nearly a quarter of them self-employed. But as she is quick to point out, there’s no paper trail—and thus no estimate—for people who change location so frequently.

The swelling population of borderless tech workers, temporary and otherwise, has nonetheless inspired the launch of numerous startups catering to a range of travelers—think WeWork’s expansion from co-working to co-living, gone global. On one end of the spectrum, working vacation spots like Surf Office, in Gran Canaria, offer private rooms and a “community vibe” to remote workers looking to hang on the beach for a few weeks without logging off. On the other, there’s the basically-illuminati-level The Caravanserai (tagline: “Roam Free”) which beginning in 2016 will offer members three communal houses with co-working spaces in Mexico City, Lisbon, and Ubud in place of a single lease.

Bruno Haid, the founder of Carvasani, has a fairly comprehensive theory about the emerging white-collar global workforce. In a Medium post earlier this year, he framed his business in terms of an overarching shift in the way we consider not just mobility, but the organization of our social lives—for Carvasani members, an emphasis on communal space will combat the design flaws of isolated suburban living. With models like his, he writes, “Life will become more transient ... The question has shifted. It’s no longer how to move to L.A., Berlin, or Bali every couple of years. It’s now: how to organize life in all those locations in the same year.”

Increased mobility and a staggering rise in tourism internationally are “shaking things up,” says Johannes Novy, an urbanist who has studied global cities including Berlin, New York, and London. “There are a growing share of people who just don’t fit into the classic category anymore of the permanent resident.” Citing the blurring boundaries between work and leisure and the high profile of co-working, co-living spaces in global cities, he anticipates a need for urban planners and policymakers to address the growing number of people who travel, but aren’t necessarily staying in town for a few days to see the big sights.

At present, Chiang-Mai is a major destination for travelers who are also working remotely. A Thai university city with a number of international schools, it tends to attract affluent and educated locals along with a sizable international community; its cafes and music culture would be recognizable to Western visitors—but you can still live there on $803 a month, according to its entry on Nomad List. As one digital nomad told me, part of Chiang-Mai’s appeal is its distinct lack of high-traffic tourist areas.

This distaste for cliche tourist traps—and hedonistic party-hoppers—is a primary concern for digital nomads; like the tech industry it sprung from, the culture is grounded in a totalizing sense of its own entrepreneurial spirit. And while full-timers like Jay Meistrich and Amy Truong won’t become the norm any time soon, the infrastructure catering to long-term travelers is growing, with the tech sector leading the charge. Members of the creative class have long flexed their purchasing power in exotic locales, but developers and engineers enjoy a particularly privileged position in an economy ravenous for their skills. “I have an unbelievable amount of job security,” admits Komissarouk, who has worked for Google and Facebook. “It’s bizarre.”

Meistrich thinks there’s room to grow. It’s only in the last three years, he says, that his life has become possible, both from a technological and a cultural standpoint—it’s as much about laptop battery life and available Wi-Fi as the industry’s comfort with remote-friendly staples like Slack. Full-time travel, to Meistrich and others like him, is a productivity tool, a lifestyle choice. And it’s just getting started: “It’s just within the past year that we’ve found out there are other people like us.”