The name Unsettled “is about turning something perceived as a negative into a positive,” Mr. Kalan said. “Everybody feels unsettled at some point. If you’re unsettled by a 9-to-5 job, then why not embrace the uncertainty?”
The concept resonated with Stacey Chassoulas, a digital marketer from Johannesburg. She joined Unsettled’s program in Buenos Aires last fall “to change the rhythms of daily life” and test the waters of remote work with her partner, Tyrone Niland. Both are 36 and love to travel, but wanted to keep their jobs and home.
“I wanted to see if it was a lifestyle that would mesh with the corporate world,” said Mr. Niland, a partner at Bramel Business Solutions, a small private equity advisory firm.
“Concepts like Unsettled are very new to South Africa’s professional environment,” but his company was supportive “as long as I could take phone calls and respond to emails,” he said.
Steve King, a partner at Emergent Research, an independent research and consulting firm, said combining work and travel was not new, but interest has been increasing. “We still don’t know how many digital nomads there are,” he said. “It’s hard to measure, but it’s pretty clearly growing at a strong rate.”
He attributed the increase in the number of remote workers to improved technology, a changing job market and inexpensive flights. The two main groups fueling it, he said, are millennials interested in taking time off from traditional work and aging baby boomers who have financial resources and flexibility.
“Humans are social beings,” Mr. King said. “It’s not easy to penetrate foreign cultures, so help in that process is hugely important.”
Resources are plentiful. They include Nomad List, a website that ranks destinations that are accommodating to digital nomads, based on factors like cost of living, internet speed and weather; and groups like Remote Year and Hacker Paradise.
“They can help make living and working wherever we want possible,” said Johannes Voelkner, founder of Nomad Cruise, who organizes two-week networking cruises for digital nomads twice a year. “A lot of people think, ‘I wish I could do this.’ But they make it too complicated — they try to change their complete lives instead of starting with a short test.”
Mr. Voelkner said he started the cruises about one and a half years ago to combat the loneliness he felt as a digital nomad. The next voyage, from Colombia to Portugal, is scheduled for May. A typical group is “very international,” he said — about 150 people from some 30 countries, their average age in the mid- to late 20s and 30s. But people in their 60s and couples with babies have sailed.
Roam, a network of co-living properties in Miami, Bali, Madrid, London and eight additional places by the end of the year, is geared to remote workers “who need a reliable base in different cities,” said Bruno Haid, the company’s chief executive. Each location has communal living areas, with meeting rooms, a co-working space and fast Wi-Fi, and offers social activities, often unique to the locale.
“It offers a much deeper sense of the local experience and is more affordable than most traditional hotels and apartments,” Mr. Haid said. (Costs start at $1,800 a month and $500 a week.) He compared Roam to extended-stay hotels popular with business travelers, but with a stronger focus on community and design.
Most guests are “freelancers, authors and creative industry types,” he said, but “we do increasingly see employees” from companies like Google or the Boston Consulting Group.
Jim Lockard, 65, and his wife, Dorianne Cotter-Lockard, 61, empty nesters, sold their California home, cars and most of their furniture just over two years ago and have been traveling — and working — ever since. They recently spent 16 weeks at Roam’s Miami location.
“We really like the co-working, co-living concept,” said Ms. Cotter-Lockard, who runs a leadership and organizational development consulting firm. Until recently, she said, they often booked accommodations through Airbnb, but internet connectivity “was hit or miss.”
Both said they enjoyed the weekly “family nights” and daily informal dinners, where people cook in a communal kitchen and dine together. “It gives us a home base and the opportunity to meet people from all over the world,” said Mr. Lockard, a former police officer and minister who now writes and coaches.
Studies show that when employees have the choice to work remotely, “business is a whole lot better” for “people, the planet and profit,” said Kate Lister, president of Global Workplace Analytics, a consulting firm that focuses on emerging workplace trends.
Gallup’s State of the American Workplace report, released in February, showed that more American employees were working remotely and for longer periods. The “sweet spot” was employees who spend three to four days a week off site; they reported feeling most engaged at work.
Mohammed Chahdi, global human resources services director for Dell, said a large percentage of its 140,000 employees already worked remotely and the goal was to have 50 percent do so by 2020. The strategy has helped the company “grow smart,” he said, by reducing its real estate and environmental footprints and retaining talented employees.
“We have data that show employees are more engaged when they enjoy flexibility,” said Mr. Chahdi, who works remotely from Toronto. “Why insist that they be in an office when it simply doesn’t matter?”
A new study, Future Workforce, released in February by Upwork, a marketplace for online work, surveyed more than 1,000 hiring managers in the United States. It found that only one in 10 believed location was important to a new hire’s success; nearly two-thirds said they had at least some workers who did a significant portion of their work from a remote location, and about half agreed that they had trouble finding the talent they needed locally.
“Remote work has gone mainstream,” said Stephane Kasriel, Upwork’s chief executive.” On-site work between the hours of 9 and 5 “is a remnant of the industrial era.”
But there are drawbacks. “Technology is just not there yet,” said Ms. Lister of Global Workplace Analytics. Many companies do not have programs to train staff members to work effectively with remote workers, and labor and tax laws can be challenging.
“But the genie is out of the bottle,” she said, “and it’s not going back in.”
Low-cost locations like Bali and Chiang Mai, Thailand, have long attracted digital nomads, but now other destinations are reaching out. “It’s one of the trends we really need to understand if we want to be relevant,” said Signe Jungersted, director for development at Wonderful Copenhagen, the region’s official tourism organization. When highly skilled people stay for extended periods, it not only promotes tourism, but also attracts business and touches off innovation, she said.
“Travel has changed,” Ms. Jungersted said. “Everyone wants to be a temporary local.”
But Mr. Niland, from South Africa, said the benefits were global.
“The opportunity to go live in a foreign city for a month and interact with the local people and experience their culture — that’s priceless to me. But culturally, we need to understand each other for the world to work,” he said. “And this is a way to achieve that.”