When 25-year-old Greg Caplan left his job at Groupon recently, he really wanted to spend some time traveling and working remotely, but ran into a few problems.

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“I was able to find remote work, but it’s difficult to find friends to travel with,” he says. “The biggest issue is traveling alone. I thought it’d be lonely. I wanna go travel but I wanna do it with a community and in a more structured way.” This predicament prompted him to launch Remote Year, which offers 100 remote workers an opportunity to travel together to 18 different locations over the course of a year. Remote Year handles logistics like itinerary, lodging, and activities. And if participants don’t already have a job that allows them to work outside the office, Remote Year will help them find one. “People really, really want to do this type of program,” Caplan says. Indeed, just three days after the site went live earlier this month, Remote Year already had more than 3,000 inquiries from potential applicants, and 15 companies expressed interest in hiring workers that they may never actually meet in person. How It’s Possible To Travel The World As You Work In the past, taking a year to travel around the world might have also meant taking a year off work. But as digital tools make long-distance communication and coordination easier, location becomes less important. And many companies already encourage remote work, like Sawhorse Media, the technology company behind MuckRack and the Shorty Awards. Of its staff of roughly 20, just half of those work in the New York headquarters. “We have people working for us from anywhere from LA to North Carolina to Canada and even Poland,” says CEO Greg Galant. “Some of them we never see. It’s an increasingly large trend because of the challenge of both finding the right talent and also the nature of work becoming easier to distribute. Half the tools we’re using didn’t exist just five or 10 years ago.” Remote Year says it will help participants find a job “in virtually any field and for any level of experience.” By working with companies to find openings for people with specialized skill sets as well as entry-level employees, Caplan says he “will help ensure there is an opportunity that fits any background and skill set.” Caplan says Remote Year will organize local adventures in each country on the trip, as well as a designated work space at each location.

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In return for serving as a de facto travel agent / employment agency, Remote Year takes a cut of its participants’ paychecks twice a month to cover the travel costs. It keeps some for itself, too, but Caplan is coy about just how much. “Remote Year will earn a small profit on the program, but the dollar / percentage is not set,” he says. “The fees will be stable for participants but costs might fluctuate.” In other words, participants will pay the same amount each month, but Remote Year’s cut of that amount will vary depending on travel costs. Some people will have to switch jobs for this, but that’s totally fine. That could be a great fruitful experience anyway. Will It Actually Work? While it seems like a cool idea, there are a lot of gaps that need to filling, and the Remote Year website contains almost no information about what is a hugely ambitious project. Indeed, some of the most important details for potential applicants are unclear and it seems that Caplan doesn’t have the answers. For example, how much will the trip cost? Caplan won’t say, but claims the minimum salary a traveler might need in order to pay Remote Year and have some leftover cash hovers around $35,000. “There’s gonna be people who go way outside that range,” he says. “People on Remote Year are not working for Remote Year. They’re a direct employee of a company.” Therefore, one’s pay will vary based on experience and type of work. Also not clear yet are which 18 locations Remote Year members will travel to. And Caplan is tight-lipped about how he’s choosing “the most interesting 100 people” out of thousands of applicants for this inaugural trip. But he does insist diversity is a high priority. “I want first of all, most importantly, diversity on the program. People from different countries, backgrounds, education, skill sets, marital status. I have a married couple that said ‘Is it possible to come if you’re married?’ I think that sounds awesome.” Of course, many married couples won’t be able to travel the world for a year, even if their bosses are cool with it. And while teleworking is indeed becoming more commonplace, it isn’t feasible in some industries. “Some people will have to switch jobs for this, but that’s totally fine,” Caplan says. “That could be a great fruitful experience anyway.” What if people don’t get along? Putting 100 strangers in close proximity (Caplan says sometimes they’ll have to share rooms) is a recipe for disagreements. The hope is that sheer size of the group will ensure everyone has a friend. And if they don’t want to participate in planned activities, they won’t have to. “They are totally free to go do whatever they want whenever they want,” Caplan says.

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Galant, from Sawhorse Media, says he’d certainly consider letting employees enroll in Remote Year, so long as they kept producing good work. “You just wanna work with really talented people,” he says. “It doesn’t really matter where they are.” But since Caplan won’t say what requirements applicants will have to meet, it’s not clear from an employer’s perspective just how talented Remote Year members will be. Caplan says he is “strongly curating” group members, but simply being chosen from a large group of applicants doesn’t carry much weight, it’s why you were chosen that’s important. Are Remote Year workers special because they have a sense of adventure? Will they boast particularly unique skill sets? Can Remote Year vouch for their work ethic? On this, Caplan says only that “the first inaugural batch is gonna be highly filtered, so it’s gonna be people that really want it.” For a company whose livelihood depends on its limited number of annual members getting consistent paychecks, Caplan seems surprisingly unconcerned with making sure the jobs are secure and the workers are reliable. “We don’t have the specific terms of the program set around canceling and situations such as losing their job, and we will handle those type of situations on a case-by-case basis,” he says. So far it’s just Caplan and his big idea, but his goal is to have five full-time employees dedicated to the logistics of looking after 100 people and ensuring each pitstop provides a suitable workspace. He’ll have to straighten out all of this ambiguity soon, the inaugural trip leaves in just nine months on June 1, 2015. The program will open to applicants over the next few months, and it sounds like a lot of people will be waiting to sign up.

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