Beyond work from home: Why ‘digital nomads’ think they’re the future of remote life


The Tulum, Mexico, location of Outsite, a co-living and co-working start-up that has become popular with digital nomads, and is betting that work-life balance will become work-tourism-life balance amid the massive shift to remote work caused by Covid-19.


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 Abroad.”

“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 Biarrtiz), “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.”

Sing uses Airbnbs for living, but as a self-described “solo remote professional,” he also pays for an Outsite membership, so he can work in a collaborative environment. “It can get lonely so community is important,” he said. The Outsite location he uses in Lisbon is “not packed,” but it is occupied by five to seven people a day.

Right now, younger professionals who travel for nightlife and bars are not going to be able to have the experiences they want, “but if you enjoy a nice meal and glass of wine and don’t need to have a bustling life, it’s great,” Sing said of his Lisbon experience. “It is a little quiet, but when you talk to the locals, they talk about how it is pleasant.”

The slower, more restricted life of Covid-19 that he has experienced in Lisbon brought Sing to a realization about a better work-tourism life balance. “When you are working, not just vacationing, it almost makes it easier to be more mundane in terms of routine,” he said. 

“I feel safe and productive and I have friends here now. … The next narrative will be you can work from not just somewhere cheaper than the Bay Area in the U.S., but the next wave is outside the US,” Sing said.

Employers and the work-from-anywhere life

Erik Dyson, CEO of the disaster relief nonprofit All Hands and Hearts, runs a lean operation and his staff were already 85% to 90% remote before Covid-19. “It never made any sense to say, ‘You’re an amazing chief marketing officer but you have to move to Massachusetts, where we have our headquarters’. It made no sense to compel people to congregate in one place,” Dyson said.

As an NGO, All Hands and Hearts also can’t offer the same money as corporations, even if it can attract a demographic of young workers from similarly desired backgrounds and mindsets. That led Dyson to look for ways to use quality of life as a way to make up for the nonprofit’s inability to compete on compensation.

“We made an early decision to embrace, as a recruiting strategy, that you can live wherever you want to live, and you will make less money, but we are mission-driven,” he said.

Almost all of its team is very young, less than 30 years-old.

Think about all-remote workers. The idea of home is great, but you still need opportunities for human interaction and ways to experience the world, whether Dubuque, Iowa or Costa Rica.

Erik Dyson

All Hands and Hearts CEO

But Dyson discovered that remote work doesn’t always even come close to working the way it should. When All Hands and Hearts brought about half of its 200 staffers to a meeting in Puerto Rico a few years ago, many revealed feelings of isolation and loneliness working from home. “It sounds great, but they missed the informal conversations. … wake up, I’m in an apartment, go to computer and work all day, teleconferencing, but don’t ever talk to people or see people,” Dyson said. “One of the big things I heard was, ‘I miss human contact with co-workers.'”

He was struck by the digital merger of the Airbnb and WeWork models when he learned about the Outsite approach — it is not the only business model of the type, with another called Selina also making a bid for young remote workers — and All Hands and Hearts decided to buy memberships for all of its non-program staff, any staff not working at disaster sites.

“We said, ‘if you miss human contact, go live in Portugal for a month, and the monthly burn is not much more than having an apartment, so go when your lease is up,” Dyson said. “If I can help people extend tenure with us, it was worth the money. If I can move someone from two years tenure to three years, that is a huge uplift, but it’s unrealistic to think they’ll do this job for seven years,” he said. “People sacrifice, including on salary.”

“Outside is not cheap,” said, digital nomad Sing who described it as a “luxurious hostel” given its cohabitation and coworking design. “It’s geared to a professional crowd that can afford it, not, if you will, the backpacker crowd.”

Outside provided All Hands and Hearts with a 50% discount on memberships, which ended up costing All Hands and Hearts roughly $10,000, “real money to us,” Dyson said. But he said the cost, even to a tightly budgeted charity organization, pays for itself when the work benefit leads an employee to stay longer.

An Outsite membership is $149 annually, or $249 for a lifetime. Members can then access any location, with local prices varying from $50 nightly (Portugal) up to $120 (San Francisco). Members receive discounts when they book a week, or a month, and in off-season or last-minute periods. Members also gain access to an online community, and as many are not travelling right now, 70% are using Outsite for the professional networking aspect, Guisset said, seeking knowledge from communities and travelers around the world about their current situation.

“We want to encourage longer stays and slower travel,” Guisset said.

Some of the more exotic locales, such as Hawaii, are still out of reach for many All Hands and Hearts workers, even with a membership. So last Christmas, All Hands and Hearts gave a $300 credit with Outsite to employees for a week in Hawaii or a month in Portugal. “We don’t give bonuses,” Dyson said.

Unfortunately, that program rolled out around February, “and then Covid hit,” Dyson said. “They have the credit sitting there and can’t travel, but I think it will come back. … They will go live there and check out places, and if you as an employer can enable me with Outsite or flights or work hours changing, I see that as a huge benefit and I know our people are appreciative.”

Not all remote workers are created equal

Dyson said as a CEO how has managed a mostly remote staff for years, he has a warning for companies swiftly transitioning to a work-from-home paradigm: not all employees know how to work remote, or work well remotely. He dismissed concerns that employees are more likely to waste time at home, and said the nonprofit’s experience offering unlimited paid time off showed that it is never the policy, but the person, that ultimately dictates success. “We never had a problem, not a single person had to be let go because of unlimited PTO,” he said.

But measurements compiled by All Hands and Hearts of employee workload indicate that not all workers are created equal when it comes to their ability to be productive in a remote environment. 

“Some people can’t work remote,”  Dyson said. “I think the big challenge is not a metric measuring the productivity of all people doing it, but finding those who can. … I spent 20 years living the corporate life and I was always traveling and I am going crazy now, six months at home. I am hearing from my team every day, everyone going stir crazy, they like to travel and are just pinned down, and European folks already started to travel because they can. … Think about all-remote workers. The idea of home is great, but you still need opportunities for human interaction and ways to experience the world, whether Dubuque, Iowa or Costa Rica.” 

The nonprofit is already seeing that desire to travel in the volunteer staff of 8,000 to 10,000 workers it brings in from around the world to rebuild schools in places like Nepal and the Bahamas. Earlier this summer, All Hands and Hearts opened bookings for a mid-Sept. volunteer opportunity in the Bahamas and it filled all the open spots for the first four months of work in a few days.

“There is a huge desire among the younger demographic,” Dyson said. “Everyone’s life has been upended, college students leaving school, taking a gap year, and people who left jobs. People being given flexibility they never had before.”  

I would like to return back to the U.S. to see friends and family, but it could be closed until 2021 or longer. … It is almost as if when I go back to the U.S., I’m kind of trapped essentially, and that’s why I’m taking the liberty … if I have all my needs met, why not stay?

Drew Sing

solo remote professional

Whether workers like Drew Sing and employers like All Hands and Hearts will cede being the exception and become the rule in the world of work is impossible to predict — like many features of a post-Covid world. But the way people outside of the existing digital nomad lifestyle are thinking about their own future is changing.

Dan Wasiolek, a senior equity analyst at financial research firm Morningstar who covers the lodging and travel sector, said when he read the recent headlines about J.P. Morgan and Ford going to hybrid work models, it hit him as being “meaningful” for an analyst who covers hotel companies reliant on properties in urban centers. But it also struck him personally, as a worker.

“As an analyst, I don’t feel like I need to be in an office to be productive, and that’s something I can measure and show it to be the case. I think there will be lots of people like me, and I wouldn’t be surprised if I’m 50% in the office permanently. And it does allow me to say, ‘OK, if I want to be in San Diego for the next five days with my family and work that Wednesday and Friday from there, and have a long weekend, it will be easier,” Wasiolek said. “There is going to be an incremental portion of workers that will be in some sort of nomad life, not work six months from anywhere, but longer weekends, or a week here and there. That seems reasonable and realistic.”

Outsite closed a post-seed round of funding during the Covid crisis, but the company declined to disclose details, and it is currently raising a real estate fund to buy distressed hospitality properties in areas it thinks will be popular post-Covid. Guisset said a lot of hospitality property managers were hoping for a good summer and lacking a sharp turnaround, will be more likely to sell properties as the season turns back to what would be dependent on business travel as vacations end.

“Business travel is in shambles and will never be the same. Some destinations and hotels will have to adapt to a new kind of tourism where people travel less frequently but stay longer,” the Outside CEO said. “When the real estate market was really high and hotels were doing really well, it was really hard to find those properties. Now it’s much easier. We’ve already seen a lot of properties going to the market at discounted rates.”  

“The tables are turned,” said Sing. “It’s odd. No one can leave the  U.S., but I’ve been given freedom to be able to maybe go back home, or go to another country.”

Sing said he would consider going to Mexico, still open to Americans, or the U.K. or Ireland, because they are not EU countries tied to the Schengen Agreement on borders and travel. Americans can still fly to Mexico, and in addition to its existing Tulum location, Outside is about to open one in Cabo.

“I did not think I would be away this long,” he said. But as it has become more difficult to just hop from place to place, “this remote working lifestyle is almost more enjoyable,” Sing said.

As for an eventual return to the U.S. from Lisbon, or another international location, Sing still owns his place in Seattle that he can go back to, but due to the circumstances, he says he is happy with his decision to be in Lisbon. “But I’m a remote pro, with a home base. It’s unique, kind of new. … I had to come to terms with a whole new world in March… I had to come to terms with being here for a long period of time. I would like to return back to the U.S. to see friends and family, but it could be closed until 2021 or longer. … it is almost as if when I go back to the U.S., I’m kind of trapped essentially, and that’s why I’m taking the liberty … if I have all my needs met, why not stay?”

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