How workation failed some digital nomads

Travellers were bogged down by Wi-Fi, lockdown, Visa permits and Tax

For a certain kind of worker, the pandemic presented a rupture in the space-time-career continuum. Many Americans were stuck, tied down by children or lost income or obligations to take care of the sick. But for those who were unencumbered, with steady jobs that were doable from anywhere, it was a moment to grab destiny and bend employment to their favour.

Their logic was as enviable as it was unattainable for everyone else: If you’re going to work from home indefinitely, why not make a new home in an exotic place? This tiny cohort gathered their MacBooks, passports and N95 masks and became digital nomads. They Instagrammed their workdays from empty beach resorts in Bali and took Zoom meetings from tricked-out camper vans. They made balcony offices at cheap Tulum Airbnbs and booked state park campsites with Wi-Fi. They were the kind of people who actually applied to those remote worker visa programs heavily advertised by Caribbean countries. And occasionally they were deflated.

David Malka, an entrepreneur in Los Angeles, had heard from friends who were living their best work-abroad lives. In June, he created a plan: He and his girlfriend would work from Amsterdam, with a quick stop at a discounted resort in Mexico along the way.

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The first snag happened almost immediately. In Cabo San Lucas, Malka and his girlfriend realized that the European Union wasn’t about to reopen its borders to American travellers, as they had hoped. Returning to the United States wasn’t an option: Malka’s girlfriend was from the United Kingdom, and her visa wouldn’t allow it.

The two decided to stay in Mexico a bit longer. At first, it was glamorous, Malka said. Working by laptop — he manages a portfolio of vacation rental properties — they had the resort to themselves. But by the second week, their situation began to feel like Groundhog Day. The city and the beach were closed, so the couple never left the resort. Meanwhile, the travel shutdown was hammering his business.

“All we could do is sit by the pool or go to the gym,” Malka said. The repetition, boredom and isolation all wore on them.

Eventually, the couple took a 28-hour, two-layover trip to Amsterdam, where Malka was indeed turned away at customs. They retreated to London, where they promptly broke up.

He has been there since. “Cold, raining, depressing,” he said. “Those are the first three adjectives that come to mind.”

Now Malka is trying to figure out how to get to Bali — it’s technically closed to visitors, but he heard about a special visa that can be rushed for $800 — or use his ancestry to obtain Portuguese citizenship. It’s a lot of logistics.

“I have PTSD planning my next month,” he said.

Malka is far from the only Covid nomad to stumble on the road. It turns out there are drawbacks on the trend stories and Instagram posts didn’t share. Tax things. Red-tape things. Wi-Fi rage things. Closed border things. The kinds of things one might gloss over when making an emotional, quarantine-addled decision to pack up an apartment and book a one-way ticket to Panama or Montreal or Kathmandu.

The Worst of Both Worlds

Americans have never been especially good at vacation. Before Covid-19, they were leaving unused hundreds of millions of paid days off. They even created a work-vacation hybrid — the workation. The idea: Travel to a nice place, work during the day and then, in theory, enjoy the scenery in the off-hours. In pandemic times, the digital nomads have simply made workation a permanent state.

The bad news is it’s the worst of both worlds. They should be enjoying themselves in their new, beautiful surroundings. But they can’t enjoy themselves, because work beckons. The anxious self-optimization pingpongs between “Why aren’t I living my best life?” and “Why aren’t I killing it at work?”

Katie Smith-Adair and her husband run PlaceInvaders, an event company in Los Alamos, California. When the pandemic halted business, they packed up their Volvo with a tent and an outdoor shower for a monthlong camping road trip around the West. All the while, she worked 40 hours a week trying to set up PlaceInvaders for virtual events.

The first lesson learned? Never trust campground Wi-Fi. The second? Expect judgment from campground workers for needing the Wi-Fi.

“They make you feel bad because you’re not unplugging and getting into nature,” Smith-Adair said. “This is my job. I want to unplug, but I also have to get on that Zoom call real quick.” At an RV park near Boise, Idaho, she noticed a Wi-Fi hot spot whose name was the equivalent of a middle finger directed at all Californians.

Smith-Adair’s office became a folding chair on the sidewalk outside whatever McDonald’s or Starbucks was nearby. It wasn’t exactly a peaceful commune with the redwoods. During one curbside conference call in Eugene, Oregon, a nearby man with a weed wacker began roaring his motor. Adair-Smith told him that she was trying to salvage her career. He didn’t care.

When digital nomads do manage to indulge in the splendours of their new homes, they can experience another, more psychic toll: the haters. Austin Mao, a short-term-rental operator in Las Vegas, posted on Facebook about escaping to Costa Rica with his wife in March and was surprised to receive a flood of angry comments. People accused of him spreading Covid. They were outraged that he had abandoned his country. One person even unfriended him.

After the haters, Mao said, came the guilt. During the pandemic, he and some friends have kept in touch via monthly Zoom calls. The conversations have a structure: The friends take turns describing what’s going well and not so well in their lives, which they refer to as their “top 5%” and “bottom 5%.” In Costa Rica, Mao would share tales of eating fish he had caught himself and diving with whales and sharks. He was living in a beachfront jungle villa where monkeys would knock coconuts from the trees, and he would chop them open with a machete, savouring the fresh juice.

His friends, who were quarantining in the United States, had no such wealth of material. Their stories rarely changed. “They would frequently say, ‘I don’t have a top 5 or bottom 5. My life is kind of blasé,’” Mao said. “It felt like I was cheating.”

After six months, Mao and his wife, Chuchu Wang, needed to return to the United States for her to keep her green card. He noticed a change: The Facebook friends who had taken out their coronavirus rage on him came around. Now, Mao said, they’re asking him how they can pull off a similar escape.

‘Intermittent Fasting of Taxes’

Perhaps the worst potential outcome not advertised by those who’ve escaped: You and your employer could end up in tax audit hell.

Lots of American travellers try to use a tax rule that carves out exemptions for Americans living abroad. But it requires being out of the country 330 full days of the year, not counting travel. Messing it up brings severe penalties.

“It’s the intermittent fasting of taxes,” said Alexander Stylianoudis, the general counsel at WiFi Tribe, a group that helps facilitate travel for 900 digital nomads. “Everyone talks about it, and everyone does it wrong.” The number of mistakes he has seen since the pandemic has multiplied, Stylianoudis said.

Some workers have avoided that by simply forgetting to mention their location to their employers — the “don’t ask, don’t tell” of remote pandemic work. Others have been honest and lived to regret it. One employee of a publicly-traded tech company went to Canada when her office closed in March. In September, two weeks after a promotion, the company suddenly told her that she had to return to the United States within two weeks or resign. The reason, she was informed, was to avoid paying foreign taxes. (She asked that her name be withheld because the situation is unresolved.)

Other employers are trying to decide where to draw the line. Leigh Drogen, the chief executive of Estimize, a fintech startup, said he had discouraged an employee’s request to bounce around from country to country for a full year but had given permission for the worker to go to Spain for six months. Estimize’s oversight of its staff is already “thin,” Drogen said, and he worried about the employee’s ability to focus while moving around.

“You work best when you’re in one place,” he said.

There are also visa issues. In years past, digital nomads would cross and recross borders as needed to avoid overstaying. That’s not so easy in a closed-border pandemic.

In March, Ryan McCumber, a business consultant, was stuck in Portugal. He had been travelling in Europe, and a comedy of errors and the sudden continentwide lockdown stranded him in a beach town, Algarve, with just four days of clothes while his dog and the rest of his luggage remained in Warsaw, Poland, a previous stop.

The pandemic made his conference business nonviable, so while in Portugal he decided to create a startup accelerator focused on sports technology. The biggest challenge, McCumber said, was not making his partners in the United States too jealous while he took calls from the beach.

Although a mugger assaulted him, giving him 15 stitches and a scar above his eye, he fell in love with Portugal’s cheap sangrias and ocean air, and in early summer, when his airline finally offered him a flight home, he didn’t want to leave. With his visa already expired, McCumber went to the immigration bureau and asked for political asylum.

“I said, ‘Trump’s a dictator, my city is burning, and people are dying,’” he said, citing the president, protests against police violence and the virus. “They made a joke that I was the first person since the Vietnam War from America to ask for that.”

The government workers laughed, he said, and then approved an extension through the end of October. (McCumber has since returned to the United States.)

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Others are struggling with the same vacation fatigue experienced by Malka, the Cabo-to-London-to-maybe-Bali wanderer. According to research conducted at Radboud University in the Netherlands, it takes eight days of vacation for people to reach peak happiness. It’s downhill from there.

When the pandemic hit, Stylianoudis, the lawyer, was on the island of Koh Phangan in Thailand. At first, he couldn’t complain about the tropical locale. Each day, after work, he swam in crystal-clear water. But after five months, he was itching to get out. He had become a regular at the island’s 7-Eleven. He even grew tired of the beach — something he hadn’t thought was possible.

The feeling of being trapped in paradise was hard to explain. “I started to feel like I was in a sequel of ‘Lost,’” he said.

‘I Just Want to Go Back Home’

This summer, Katie Jacobs Stanton, a venture capital investor living in Los Altos, California, saw her moment for a fresh start. She was about to become an empty nester, with two children in college and another taking a gap year. Her father had died of Covid, and being alone at home, especially amid California’s wildfires, was too depressing. Figuring she could find venture investments and strike deals from anywhere, she decided to take a gap year of her own.

In August, Jacobs Stanton gave away most of her possessions, bought a Tesla and prepared to hit the open road with Taco, her golden retriever. “I had this image of a glorious, beautiful American landscape and mom-and-pop, Main Street USA,” she said.

She found a different reality. First, someone stole her Tesla. (The police recovered it.) Then her first stop, Reno, was grim. “It’s a very sad city,” she said. In Tahoe, wildfires raged. In Bozeman, Montana, Taco became sick. A trip to a veterinarian led to emergency surgery; Taco had eaten a tube sock.

Then came Kanye West. In September, Jacobs Stanton had a phone call with the hip-hop artist about a possible venture in the music business, which he mentioned on Twitter. Name-checking her set off “one of the most bananas days in my life,” she said. Jacobs Stanton was overwhelmed with messages, but on the plus side, the episode prompted all three of her children to call and check in.

She froze while camping in snowy Yellowstone and stressed over the icy roads. Then her daughter in college got the coronavirus, and Taco needed more surgery. (Both recovered.) On top of it all, people in small towns she visited didn’t wear masks and were hostile about it.

By late October, she was ready to call her gap year short. “I think I just want to go back home,” she said. “No more road trips for Katie Stanton.”