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How the digital nomad went into business


The romantic dream of becoming a “digital nomad” is almost as old as the internet itself. Steven K Roberts – a pioneer who rode a computer-controlled bicycle across the US more than 30 years ago – wrote in 1994 about creating a “Virtual Technomadic Flotilla . . . of travelers around the world” based on the fact that ” physical location becomes irrelevant once you move the essence of your life to the fumes of the net’.

But it wasn’t until Covid-19 that the term really took off. The pandemic created the perfect conditions: workers wanted a change after the boredom of the lockdowns; companies had realized they could rely on staff to work remotely; and tourist-dependent countries were desperate for visitors. Suddenly it seemed possible for any white-collar worker to work wherever he wanted – not just freelancers, some of whom already did, but regular employees as well. Dozens of countries launched “digital nomad visas” to formalize and capitalize on the trend.

Unfortunately for the romantics, that dream of freedom has collided with the realities of taxation, immigration, cybersecurity and labor laws. Companies haven’t killed digital nomadism for the masses, but they’re wringing it into a less risky and more controlled form. In other words, digital nomadism is becoming independent.

Companies that want to keep their workforce happy have “started thinking about how to incorporate this into their employee value proposition – they want to control it, but they want their employees to feel like they’re getting something in return,” says Claire Pepper of Vialto Partners, which advises companies on cross-border global mobility issues such as immigration, tax, travel, payroll and remote work.

That generally means telling employees they can temporarily work from an international location, but with restrictions on where and for how long. Pepper says companies will often “re-draft some countries that are high-risk in terms of cybersecurity (or corporate tax)” and “have a shortlist of favorable locations.” The most common allowed time frame is 20 to 30 days — the safest way to avoid tax problems. When Vialto polled more than 800 companies about their remote work policies last year, only 7 percent supported it for more than 60 days.

Some go a step further and make agreements with specific locations. Technology company Cisco recently sent 17 employees to Rhodes for three months in collaboration with the local government there. The staff worked remotely from the island, but also participated in volunteer activities – an effort to demonstrate that digital nomads can benefit the host community and don’t have to be closed off and aloof.

It’s a reasonable concern to have. There are already raging noises coming from places like Mexico City and the Portuguese island of Madeira, where digital nomads are being blamed for driving up real estate prices and attracting Instagrammable cafes with fast Wi-Fi and fancy coffee, rather than learning know the locals. Meanwhile, the OECD wrote last year that the “host benefit of digital nomads remains unclear.” In most countries, digital nomads would only become tax residents after 183 days, the OECD stressed, and are usually not allowed to participate in the local labor market, meaning their main contribution is simply consumption.

Gianpaolo Barozzi, an HR director at Cisco, told me that “the typical digital nomad is the freelancer, the website developer who can develop from anywhere, but what we’re experimenting with — which is much more powerful for the place hosting — are these corporate digital nomads… We didn’t send three people, we sent seventeen, so there’s a certain critical mass. Those people have a certain common identity.”

Of course, Cisco has every interest in the continued popularity of remote working, but it seems like a worthy and interesting experiment nonetheless. More generally, I think it’s a good thing that companies have staff temporarily work elsewhere. However, I’m not sure you can really call it “nomadism.”

In contrast, last week I spoke with Lucy Rogers, a scientist and engineer who is writing a book. Last year she thought, “If I work from my back bedroom, why not do it everywhere?” She packed her belongings into storage, rented out her house for a year and went to Chile where she stayed with a local family and took Spanish lessons. Now she is on an island in Thailand.

“I’m going to torment you,” she said mischievously, before turning her laptop over so I could see her view—an azure sea and a swaying hammock. Call me an old romantic, but that’s what I call living the true digital nomad dream.


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