Work-from-home policies have allowed employees to log in from their living rooms in their pajamas, but some workers have taken the idea to an extreme, secretly logging in from across the world while keeping their bosses in the dark.
It can be a tough charade to keep up. A marketing specialist based in Chicago who since 2020 has secretly lived in more than five countries while working 9-to-5 jobs recalled joining a Zoom meeting from Colombia as his coworkers lamented a recent storm that had covered the Midwestern city in snow.
“I need to go to the beach right now,” he recalled a coworker saying. “I’m so tired of this awful weather.”
“Yeah, I really want to go to the beach. This is so terrible,” the marketing specialist replied.
Little did his snowbound compatriots know he was actually a 10-minute walk from the Caribbean Sea and had just returned from an outdoor yoga session.
He’s one of four remote workers interviewed by Insider who have secretly worked abroad without their employers’ permission. They spoke on the condition of anonymity, but Insider has verified their identities and their employment status with documentation.
They say one trick to avoid getting caught is reading the local news and tracking the weather. The marketing specialist said these two best practices helped him maintain the ruse — during which, he says, he earned a pay bump and a promotion. His social-media accounts are public for work, so he posts pictures of his travels only in private Instagram Stories limited to close friends.
When the specialist’s company required staff to return to the office earlier this year, he found a new remote job at a nonprofit. He said that even though this employer would likely be more lenient, he keeps his international adventures hush-hush.
“I went paragliding in the Andes Mountains. I went to a desert in Peru and went sandboarding,” he told Insider. “After doing all that, I just wasn’t going to go back to the office.”
Over the past two years he’s traveled to Panama, Peru, Colombia, Ecuador, the Dominican Republic, and Mexico. He said he still pays rent for his apartment in Chicago and subleases it to friends when possible. But even in the months he has to pay rent, he said, he spends less money than he did working full time in the Windy City because other things cost less.
For some, traveling full time is indeed more affordable than living in the US.
A former Miami resident told Insider that after his rent was raised to $2,700 a month from $2,150, he and his husband quit their in-person jobs and moved to South America. Once they set up shop in Ecuador, they both accepted fully remote positions in marketing and consulting so they could covertly travel. He said that now their housing costs average about $500 a month for two-bedroom Airbnbs.
The positions required them to be based in the US, but they didn’t divulge that they were actually traveling across the world. The couple’s new employers and coworkers believe they still live in Miami.
The former resident said they even paid over $1,000 for flights to pick up a work laptop from their former Florida address. But he said that one-time expense was nothing compared with the money they’re saving, adding that they’d been able to put 75% of their income toward paying off debt, a financial burden that had made them feel weighed down back in Miami.
“If we tried to do the exact same thing in Miami, as far as paying off our debt that rapidly, we’d be literally living on ramen noodles,” he said. “We can get lunch for $2.50 every day. The exact same plate of food in Miami would have easily cost you between $12 and $15.”
He said that while the arrangement had made for some awkward encounters with coworkers, who’ve asked on multiple occasions why he’s wearing a windbreaker in Florida, the financial savings are worth it.
When coworkers ask how his weekend was, he said he contrives scenarios based on the couple’s past life of brunching and beaching, when in reality they bathed in volcanic hot springs and hiked through the Andes.
But some scenarios are impossible to prepare for, like the time in July when their Airbnb in Ecuador started shaking from an earthquake in the middle of a client meeting.
“Do you know what Florida doesn’t have? Earthquakes,” he said, adding that he told the client that he was “temporarily” in South America, and they didn’t think much of it.
A Berlin-based remote worker at a multinational tech company who has secretly worked from the Canary Islands and Portugal told Insider the key to pulling the scheme off had been respecting his colleagues, working hard, and resisting any urges to show off.
“I didn’t tell anybody, even colleagues who I’m friends with outside of work,” he said, adding that he doesn’t have any social media. “It doesn’t feel the best always, but that’s the only way I can maintain this lifestyle.”
He said he uses his personal computer with a VPN to ensure the company can’t track his location and always has the computer’s clock set to Berlin time in case he has to spontaneously share his screen. He said he’s also aware of any background noises that could give away his location, like the tropical birds in the Canary Islands.
“There’s no birds in Berlin chirping in the middle of winter,” he said.
In the summer he returns to Berlin and works from the office about three times a week — an option he said he values as much as his ability to work remotely.
“I really like my job. I really like my team. That’s why I don’t want to necessarily quit,” he said. “But I like my job because they don’t ask so many questions — because it’s flexible. So those go hand in hand. As soon as they remove that, it’s not worth keeping anyway, so if they fire me, it doesn’t matter.”
While many companies have allowed employees to work remotely full time, most do not permit working internationally because of regulatory concerns and risks regarding taxes, insurance, immigration law, and cybersecurity. It can also create compensation concerns for companies that calculate pay with the local cost of living in mind.
A software engineer from Minneapolis who attempted to work virtually from Puerto Rico this winter said that even though he was connected to a VPN, his company’s IT team reported that his IP address was coming from outside the US. He said he got a stern message from his team’s director, who told him to get back to the States immediately.
This spring he left the company for a tech startup with more lenient international-travel policies.
“My general philosophy is it shouldn’t matter where I’m working,” he told Insider on a video call from Spain. “As long as I’ve been exceeding expectations, who cares if I’m in Spain or South Africa or Minnesota?”
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