How to Work Remotely—In an Exotic New City Each Month

LIFE WAS GOOD for Krista Jancik. At 35, she was working as an art director at an advertising agency and living in the trendy West Loop neighborhood of Chicago. Still, she said, “Everything was feeling a little too routine.” Initially, Ms. Jancik considered planning a big vacation—China, maybe, or Australia—but then she came across an ad for Remote Year: a fledgling travel company that spirits groups of remote workers away on a year-long journey around the world. Though Ms. Jancik’s job was not conceived as a remote position, within weeks, she’d sold her company on the benefits of such an experience, broken her lease and boarded a plane to Malaysia. Now, she lives in a new city each month—Kuala Lumpur, Prague, Marrakesh—and fits in island-hopping excursions in Thailand or camping trips to the Sahara around her normal workload. “I feel constantly in motion,” she told me via video chat from Belgrade, Serbia. “I feel more productive, more active, more creative.”

Long-duration travel has historically been the purview of backpackers roaming the hostel circuit, or a class of moneyed jet-setter with no apparent need for a regular paycheck. Recently, though, a new crop of companies has emerged with the aim of helping working stiffs take their jobs on the road. 

Remote Year, the leader in the field, was started in 2014 by two Chicago roommates, a strategy consultant and a venture capitalist. On a whim, the duo posted an ad online broadcasting the opportunity to work remotely and travel with a community; within a month, they had collected 50,000 email addresses. “We realized we were onto something,” said Sam Pessin, one of Remote Year’s co-founders. The company scooped up $12 million in venture funding in 2016, now has teams on the ground in 14 cities around the world, from Cape Town to Medellín, and will put 10 groups of around 50 travelers on the road this year. 

For a $5,000 lump sum and fees of $2,000 a month, Remote Year provides its customers with a year’s worth of flights from city to city, and everything they need to hit the ground running in a new locale: a place to live, a co-working space and local staff for troubleshooting and sightseeing tips. The company also hosts regular social events, like wine tastings or neighborhood walking tours. One month, you might find yourself taking surfing lessons in Lisbon. The next, zipping around Hanoi by moped.