These remote employees are secretly working abroad

Whenever I set up interviews with this one source — we’ll call her Laura — I notice something funny. She always scheduled our calls in Central Time.

“Yeah, because my computer is scheduled in Central Time so that anytime someone asks me a question that’s work related I check the time on this tablet,” she said.

We’re concealing Laura’s real identity because her employer thinks she’s in Tennessee. She’s actually living in Portugal.

“I have this very nice apartment with this beautiful view over a river and this big balcony room made of windows,” she said.

Laura works in tech and has been living in Lisbon for a little less than a year. Portugal offers a flexible remote work visa. She wants to work there, in part, because her American dollars go further. Laura makes about $50,000 a year.

“Yeah, I could live in Memphis with that,” she said. “But in Portugal, you know, if someone’s like, ‘oh yeah let’s eat at this restaurant,’ I don’t even think twice about it. I just kind of go and do whatever I feel like.”

Of course, these aren’t details she shares with coworkers. She doesn’t talk much about her personal life at all because she’s worried she’ll slip up. 

“If I accidentally talk about the fact that I don’t drive anywhere or that I’m going to the beach and stuff like that, so I just avoid it,” she said.

Laura has met plenty of other digital nomads secretly working abroad. And there are Reddit threads to prove it. People share tips about using a VPN to conceal their location. And they keep up with local weather so they know to commiserate about the snow in Chicago, when they’re really on a beach in Brazil.

These workers take the risk because more and more, fully remote work doesn’t mean free for all. Many companies, like Airbnb and Instacart, require employees to be stationed within the United States (or the country in which they were hired).

“There is some prohibition now on just being able to work from everywhere,” said Sarah Dick, a vice president at Gallagher, a consulting firm that helps businesses strategize their work abroad policies.

That’s because working abroad comes with complications. Big ones, like what if a war breaks out? Medium ones, like taxes, insurance and data security. And small ones, like tech support.

“You can’t just, you know, run over to the local office, get your laptop turned in and get a new one,” she said.

Plus, working from abroad isn’t all fun and games. For one, there’s loneliness. It’s hard to make friends when everyone’s at dinner and, because of the time difference, you’re still tied to your desk.

“People think ah, it’s going to be great. You know, live by the sea and work for six months on my own,” she said. “But the reality is that adjustments are harder than you think.”

You know what else is harder than you think? Actually pulling off the super secret mission of living abroad. Take it from another worker we’ll call Matt. About a week into his undisclosed trip to Mexico, he got busted.

“I’m at the co-working space and I get a call from my manager. Where are you?” he said.

It turns out IT flagged suspicious activity on his computer.

“In about 30 seconds I fessed up to where I was,” he said. “They demanded me to come back with my laptop within 24 hours.”

And then, he was fired. 

A story like this might end with Matt learning some lesson about how lying always catches up with you. But … he is at it again. Matt works in data analytics and his new employer thinks he’s in Washington State. He’s actually rock climbing in Canada. 

Why hasn’t he come clean?

“I think it’s maybe, there’s a risk that if I do ask they’ll say no,” he said.

He doesn’t actually know if his work won’t let him live abroad. To stay in Vancouver he’ll need a work visa, which would require employer approval.

“I probably should,” he said. “I just haven’t had that conversation yet.”

What’s the saying? It’s easier to ask for forgiveness than it is to get permission.