Certain roles and industries lend themselves to a rootless existence – think software engineers, the startup crowd, or even accountants and consultants. “But I’m not saying your commodities trader at JP Morgan can do this,” warns Mr Matt Bradburn, co-founder of People Collective, a London-based HR consultancy that focused on advising startups. Blue-chip corporate culture only flexes so far, even in extreme times. “There’s still not enough interest at the top of big banks, say, for it to happen,” Bradburn adds. As he also points out, many firms have strict rules about where data can flow, which may also be a barrier to nomadism.

Some of the stricter employment contracts out there will stipulate where a job can or cannot be carried out, which may throw up a tricky hurdle for the would-be nomad. Many companies that don’t normally specify are now racing to redraw contracts. “Often it’s just HR departments being hesitant,” says Ms Summer Bishop, a corporate travel agent who, with her partner Mr Alexander Stylianoudis, is currently working from an Airbnb in Malta. “As long as you can represent yourself and show you can handle yourself, it’s worth pushing back.”

The web is awash with stories of influencers being shamed for sharing their beachside Dubai locations while the rest of us hunker down at home. It might pay to be sensitive while considering your background on a video call. Some luxury resorts report growing requests for indoor locations with blank walls. “I certainly wouldn’t take a call from a beach bar,” says Alexander Stylianoudis, who has been working from dozens of countries for the past four years as a legal and financial executive at WiFi Tribe, a community of remote professionals.

Striking out alone or even in a couple may be too daunting a proposition, which is why specialist companies will act as digital nomad agents. Remote Year, a community-based travel company for nomads, offers packages that take care of everything from flights to weekend activities. “It also means you’re straight into a community of like-minded people,” says Mr Shaun Prime, Remote Year’s CEO.

Don’t even think about travelling into a country in a higher state of alert, even if local restrictions permit you to enter. Do your research first and play it smart.

Even if travel restrictions lift where you live, think twice before bowling into another country (to avoid breeding resentment, apart from anything). “Always act in line with the highest levels of guidance, be it wearing a mask in public even if local rules don’t require it,” Prime says.

It ought to go without saying that time zones are an issue if, say, your clients are on the other side of the world. Your beachside Airbnb might feel slightly less inviting when you rock up at yet another 3.00am Teams meeting.

Standard travel insurance policies are rarely going to cut it for remote work, but don’t dream of going without cover. “Remote workers tend to be out doing things more, so are statistically more prone to injury,” says Stylianoudis. Work insurance policies may also limit days of cover out of a home country. New services such as SafetyWing and World Nomads have begun to fill a gap in the market. Check pandemics are included in your policy, wherever you get it.

Travel insurance is one thing, but for an added layer of protection, consider joining a remote assistance hotline such as International SOS (or ask your employer to sign you up).

The need for a visa is one of the more vexed questions facing the would-be nomad. “I think there are two camps – those who think working remotely one can do anything anywhere whenever one wants with no constraints, and those who think it’s illegal and impossible,” Stylianoudis says. “It’s more complex than that.”

It also depends on myriad factors, from the law in respective countries, to the length and nature of a stay. In many EU countries, 90 days is the standard limit for permissible remote work without a work visa, while in Thailand, for example, you technically need a work visa on day one. The key is to fully research your destination and don’t assume you can wing it.

Often (but not always), you’re fine without a work visa if the work you’re doing – and the company you’re doing it for – has no stake in the country you’re in. “But then it might become an issue if, say, that company has an office in the country and you visit it,” Bishop says.

Any nomadic worker is going to fall somewhere on the tax spectrum between double (taxed in a home and current country) and nothing. Paying no tax is a tricky feat to pull off (nor commendable for a global citizen), but there are ways to avoid getting stung at both ends. “As a rule, just assume you need to pay tax in the jurisdiction you’re from,” Stylianoudis says.

As with visas, careful consideration is required to determine tax responsibilities in the country that you’re working in, depending on its rules, the length of your stay, and the type of work you’re doing. If you’re there under three months, you may be OK. Either way, get an accountant who’s used to these kinds of variations.

If you were away from your home country long enough, you may be able to prove that you’re no longer resident and therefore not liable for tax. But there are big pitfalls for the pure nomad, from losing welfare to the vote.

Tropical paradises stripped of tourism income have raced to market themselves to remote workers with good deals on digs and visas. Barbados has a tax-free scheme with a 12-month visa for $2,000, for example.

Being paid $200k in San Francisco isn’t the same as being paid $200k on Koh Phangan, and it would be naive to expect a big salary to follow you if your employer knows your living costs have plummeted. “Working out salaries is one of the things we do for companies and we always build in geographic waiting,” Bradburn says.

Bradburn says groups of like-minded nomads are clubbing together to rent better digs, via Airbnb for example, creating ad hoc workspaces in the process. “We’re going to see more groups of, say, five or six software engineers renting a chateau in the south of France cheaper than they could each get apartments,” he says.

As home workers have found by the million, losing the time it takes to get to an office doesn’t necessarily reduce the time burden of a job. “Sometimes, I feel like we work more because you don’t put away your office,” Bishop says. “It’s always there.”

Virtual tethering can feel as oppressive as the need to be in an office, especially when – as many companies now do – a Slack or Zoom channel remains constantly open with management. “Slack is our main social network now,” Bishop says.

Nomadism favours the relatively carefree as well as the brave, but having children isn’t necessarily a barrier (especially if they’re pre-school age, and/or you’ve got money to throw at childcare). Just be sure the kids are part of or central to the lifestyle change, rather than baggage.

Even before the pandemic, coworking culture was blossoming in many desirable destinations. Think superfast Wi-Fi, desks and communal space with, say, beach attached. Cities such as Lisbon have always led the way, while places like Puerto Escondido in Mexico and Koh Phangan in Thailand have good reputations.

Hosts often favour longer stays, particularly in destinations that are known for remote work. “We always contact the host directly to negotiate a lower price,” Bishop says. Be sure then to proceed with the booking with the new rate via the Airbnb platform to retain various consumer protections.

It doesn’t matter how suitable a property looks if the Wi-Fi is dodgy. And don’t always take a host’s word for it. “Lots of places are also listed in Booking.com, which allows you to review Wi-Fi specifically, so I’ll often do that and then go back to Airbnb to book,” Bishop says.

We’ve all stayed in holiday rentals with, say, three cheese graters and no saucepans. Message your host to make sure you’ve got what you need.

“It’s so easy to fall into the tourist mindset and go out for dinner every night and buy every fruit in the supermarket on your first day in a new place,” Stylianoudis says. It’s important to rest, and – unless you’re raking it in – not to blow your income and more on expensive trips every weekend.

There are loads of ways to network on the road but Bishop says Facebook groups are the best way to get advice and find out what’s going on – and in English. “Just search, say, ‘Lisbon digital nomads’ and join the group with the most followers,” she says.

There’s roaming and there’s roaming. Go buy a local pay-as-you-go Sim card as soon as you arrive in a new country to keep your mobile bills down.

When Wi-Fi’s tricky, a mobile router is a great way to get faster and cheaper web access than a mobile data network will allow.

Bishop finds space for some fairy lights in her luggage – something to hang in each place that becomes a symbol of homeliness in a mobile world.

“I used to do five-a-side [football] when I lived in London and assumed I’d have to give it up, but I kept joining sides while I was travelling before Covid,” Stylianoudis says.

Stylianoudis and Bishop travel with only a carry-on each to carry clothes and basic supplies. It’s not that they couldn’t lug more around for long stays, but, Stylianoudis says: “It’s nice to become a lot less materialistic.”

Digital nomadism is a form of travel and therefore sustainability should be a priority. “And that means giving back to the community you’re in,” Prime says. “Buy local, talk to local people and leave a positive footprint when you move on.”