Luka Kacil, a tech entrepreneur from Slovenia, works remotely at a rooftop lounge during a Hacker Paradise trip in Da Nang, Vietnam. (Photo: Casey Rosengren)

Cassie Utt is about to spend an entire year traveling the globe, a trip that will include month-long stops in 12 exotic locales like Dubrovnik, Croatia, and Ko Tao, Thailand. To get ready for her world tour, the 24-year-old has donated her couch and her bed, put the rest of her stuff in storage, and turned in her car that was coming off lease. She's worked on visa logistics, figured out a mobile phone plan that will let her stay in touch worldwide and tried to reassure her somewhat nervous parents.

But one thing she hasn't done is say goodbye to her company.

For the next 12 months, Utt, a project manager in the hydraulics division of Eaton, will continue working for the big manufacturing company through a new outside program called Remote Year. "Quite a few of my friends are going through this right now, where they're taking a year off to travel," she said. "To have me come along and say I'm going to travel the world and keep my job? It's hard for them to believe."

The brainchild of 26-year-old entrepreneur Greg Caplan, Remote Year is something of a tour operator for professionals with wanderlust. Or as one participant described it: "like Semester at Sea, but for grown-ups with jobs."

The program, which just kicked off its inaugural trip on June 1 in Prague, is evidence of the evolving landscape of work. Increasingly, professionals with dreams of traveling the world have options beyond applying to a huge global company with offices everywhere or quitting their job for a gap year. As working remotely has become not only more technically viable but more professionally accepted, a growing crop of travel operators have tapped into this new market opportunity.

Remote Year, for example, runs participants $27,000 for the year — $3,000 paid upfront, and then $2,000 each month. In exchange, it books and covers the cost of housing in each city as well as travel insurance and travel logistics between the year's 12 stops (though participants buy their flights to and from the first and last cities). The program also secures work hubs with wi-fi in each locale, and plans events and meals to foster a sense of community among the 75 participants.

Utt and her fellow "remotes," as Caplan calls them, include entrepreneurs, plenty of software developers and designers, freelancers, and corporate employees who received blessings from the likes of Microsoft, HP, Polycom and Google to take their jobs on the road. Perhaps helping their case: Unlike traditional travel companies, programs like Remote Year have a strong element of professional selectivity.


Remote Year workers at a co-working space in Prague. (Credit: Greg Caplan)

Caplan said the early pool included some 25,000 interested folks, who went through an initial screen for income feasibility and past experience with remote work. Roughly 1,500 turned in formal essay applications, and Caplan and his small team interviewed nearly 300 to whittle the pool down to the final 75. They looked for people who would add diversity to the team and would have a high likelihood of success working remotely from all corners of the globe, since full-time work was a prerequisite.

"We didn't want to take people who just wanted a vacation," Caplan said. "We were looking for people who wanted to advance their careers with new experiences. That's a really important difference. They are all committed to growing professionally." 

There are, of course, plenty of digital nomads living "location-independent lifestyles" who have found their own way to work while traveling the world. Jay Meistrich, for example, left a job at Microsoft and then built his own start-up while jumping from one global outpost to the next, taking walking tours and lunching near castles in between software development sessions.

While such do-it-yourself arrangements have also become more viable, thanks to technology, there are those who prefer a more structured, coordinated experience — one that feels less like a solo quest and more like a global professional rotation they can pitch to their employer.

Hacker Paradise, which just started its third "batch" of trips less than a week ago in Tallinn, Estonia, provides co-working spaces and optional accommodation logistics for the roughly 30 tech workers, freelancers and entrepreneurs who compose its month-long trips. Others are planned this summer for Barcelona and Berlin, and participants pay a program fee of $850 for a month in one location, which does not include housing or travel costs.

Part of what it offers traveling professionals, in addition to help with the logistics of working from another country, is some sense of career support once they get there. Hacker Paradise has weekly lunches for participants to share their productivity goals, presentation days, and workshops on topics like negotiating or shaping a business idea.

While none of those sessions are mandatory, their aim is to motivate or hearten people who suddenly find themselves without the usual office routines, familiar time zones or cultural touch points. "It's just enough structure to know you're not just out there by yourself," said Alexey Komissarouk, one of the co-founders.

That kind of structure isn't just attractive to remote workers, but to the companies that agree to let them go. While many of Remote Year's participants are self-employed or work for companies with fewer than 10 people, Caplan said 35 of the 75 attendees come from larger companies.

While some employers were surprisingly keen on the idea, others remain a harder sell. Both Hacker Paradise and Remote Year have seen a few candidates bow out because they ultimately couldn't get corporate approval, whether from their own bosses or from HR and accounting. Others, though they finally got the okay, had to go through a long process of company box-checking.

Knowing Utt wasn't going to be the one responsible for details like finding reliable wi-fi service or a quiet place to work, however, was reassuring to Bonnie Smith, a senior vice president at Eaton who supervises Utt's boss. The clear professional orientation of Remote Year, as well as the structured access to work environments, Smith said, "offered comfort to me. She's not going to be using work time to figure it out herself." 

Smith also likes the idea of Utt being exposed to tech workers from other fields. "She's going to be working with people who surely will broaden her horizons," Smith said. "I expect her to come back with observations of how other countries do things — things we may be able to do, too."

Hacker Paradise's Komissarouk said he's even heard from a startup and a biotech company with a few hundred employees that are interested in offering his trips to workers as a company-paid perk. "Over time, we’ve been seeing more companies okay with this, by either granting them a sabbatical or letting them work remotely," Komissarouk said. "People are willing to do [things] to retain highly qualified employees."

Lindsay Daniels, who works in communications for San Jose, Calif.-based Polycom, said it wasn't hard to convince her boss after she got accepted to Remote Year. Not only had she worked in California while he was based in Singapore during her first four months in the job, her company makes video conferencing and conference call equipment. "This is what we live and breathe every day," she said.

Utt, meanwhile, thinks timing helped her get the thumbs up. She was just finishing a two-year rotational program at Eaton, and was about to start looking for her next role there when Remote Year came up. She had been interested in finding a position in Europe, but instead went to her boss with a business plan to show how her year of globetrotting could help the company. She would get a close-up view, she offered, of some of the company's many worldwide locations by paying visits to local sales offices or plants. "And if I'm working next to someone from Microsoft or Google," she said she told them, "it's a way for us to see different ideas."

For all the planning, there is still the unexpected. What happens if the wi-fi goes down? (Caplan said they have redundant Internet connections, as well as back-up hotspots.) Or if someone loses their job in the middle of the trip? (Remote Year has a $2,500 early exit fee, but hopes the group would rally to help the person find work for the remainder of the trip.) Or a laptop breaks in the middle of Vietnam? (Caplan said he doesn't offer tech support.)

Of course, another big question is what happens when Utt's or Daniels' colleagues get the same idea. Smith said she was comfortable with Utt going because she knew she was a high-performing employee, and she trusted her to work the late night and early morning hours Utt will need to put in when she's on the other side of the globe. But "can I have 80 percent of my employees doing this?" she said. "No."

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