Workers with wanderlust have new options for how to keep their job and travel the world
Cassie Utt is about to spend an entire year traveling the globe, a trip that will include month-long stops in 12 exotic locales such as Dubrovnik, Croatia, and Ko Tao, Thailand. To get ready, the 24year-old has put just about everything she owns in storage, turned in her car that was coming off lease, worked on visa logistics, figured out a new mobile phone plan 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 this week 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. The program also secures work hubs with WiFi 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 such as Remote Year have a strong element of professional selectivity.
Caplan said his program received roughly 1,500 formal essay applications, then interviewed nearly 300 people to whittle the pool down to the final 75. The program looked for individuals 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.”
Hacker Paradise, which just started its third “batch” of trips this week 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. Other trips 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 Hacker Paradise offers these professionals, in addition to help with the logistics of working from another country, is some sense of career support once they get there. The program has weekly lunches, presentation days and workshops on topics like negotiating or shaping a business idea.
While not 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.
Knowing Utt wasn’t going to be the one responsible for details like finding reliable WiFi service or a quiet place to work 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.
Lindsay Daniels, who works in communications for San Josebased 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 on the job, but her company makes video-conferencing and conference-call equipment. “This is what we live and breathe every day,” she said.
For all the planning, there is still the unexpected. What happens if the WiFi goes down? (Caplan said his program has redundant Internet connections, as well as backup hotspots.) Or if someone loses their job in the middle of the trip? (Remote Year has a $2,500 early-exit fee.) 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’s colleagues get the same idea. Smith said she was comfortable with Utt going because she knew she was a highperforming 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.”
Luka Kacil, who runs his own tech company, has been traveling to different places around the globe with Hacker Paradise since the program began last year. He’s seen here in Da Nang, Vietnam.