, Small Town Man Living the Big WFH Nomad Lifestyle

 With much of the professional world shifting to remote work and widespread acceptance of the concept among previously skeptical corporate management, the traditional idea of work-life balance is being pushed in new directions, including a concept of remote work-life-tourism never before imagined.

Drew Sing, a fully remote growth product manager at a technology start-up, has been living and working from Lisbon, Portugal, since the beginning of March, after a few months in London. He had planned to fly back to the U.S. in May, and had even booked three flights back, each with a 24-cancellation policy, but when he looked at the Covid-19 trends in the U.S. versus Europe, “each day I spent here I said, ‘I think I will stay.’ I think this is a safe place to stay during these unprecedented times.’”

Sing is not new to the digital nomad lifestyle. He left the Bay Area in 2018  to live a remote life, and bought a home outside Seattle — which he rents out, but where he maintains a basement apartment for himself — and a sleeper van in which he can travel within North America and work remotely when he is there.

“I realized that I could work from co-working spaces, and live the nomadic lifestyle,” said Sing, who just published a book on how to work a remote job from anywhere, titled, "Work From Abraod"

“There are lots of books on traveling and exploring the world on a budget, but not on continuing a career and being a productive employee while living from anywhere,” he said.

Digital nomads: From niche to next to normal 

Despite international travel limitations, Emmanuel Guisset’s start-up Outsite — which offers professionals co-living and co-working spaces around the world in locations including Hawaii, Mexico, Portugal, Bali and the U.S. West Coast — is betting that what is called the “digital nomad” lifestyle is bound for mass adoption in a post-Covid-19 world.

“Before the pandemic, we were fitting a niche of people ... nomads, freelancers, tech workers. Because they can work remotely, they choose to live a different lifestyle,” said Guisset, who is founder and CEO of Outsite. But now his business is discovering more individuals looking for a long-term stay.

Opportunities to work remotely from anywhere in the world are currently limited. Within the U.S., cities and states have banned short stays in vacation rentals, including in Tahoe and Hawaii, areas where Outsite has locations. In many European and other international destinations, a U.S. passport has transitioned from long-time advantage to handicap. And there are many mandatory quarantines around the world once a traveler arrives at a destination.

Outsite’s Bali location is closed because there is no local tourism for it, and its Costa Rica location has only a few locals from the capital city of San Jose, as well as American ex-pats. But the European locations, especially the coastal ones (Ericeira and Biarritz), “are full with Europeans and a couple American ex-pats,” Guisset said.

Some countries are encouraging foreigners, including Americans, to come on special visas to spur their local economies, such as Barbados, Estonia and the the country of Georgia. And people already are traveling within the pandemic limitations wherever possible, Guisset said. The quarantines, in fact, are leading to longer stays. “Travelling now is much more difficult so people want to stay longer to make it worthwhile,” he said.  

Outsite is seeing professionals breaking leases in U.S. locations, spurring demand for longer stays in outdoor-oriented and beach locations like Tahoe, Santa Cruz and San Diego. “They want to live in cheaper, smaller cities, closer to the nature,” he said. 

How to become a worker of the world

Digital nomad Sing’s basic points of advice: workers need to start with an understanding of their job and hours and time zones. Working North American hours has meant Sing never considered Asia. “I’ve done the math on when I would have to work and it would be difficult,” he said.

When thinking about working from abroad as a North American professional, certain continents and areas make more sense: South America, Central America and Western Europe.

“Newly remote professionals still need to abide by hours, which is fine, but it is not hard to work from 1pm -9pm or 2pm-10pm in Europe. You’re free when people are at dinner, or you can go to a cafe in the morning, and that  can be a beautiful lifestyle,” Sing said. And for remote professionals who are not on a specific company clock, “it opens up everywhere.”