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…