Though some workers have already returned to their offices after a year spent at home, many companies plan to allow at least some of their employees to continue working from anywhere, indefinitely. Twitter, Microsoft, Slack, and Reddit, for example, are just some of the organizations presently offering remote work for the foreseeable future. And as borders, both domestic and international, start to reopen, some are looking to change their definition of “home” accordingly.
We asked people who have been working from anywhere they want—a van in Moab, Utah; a long-term Airbnb in Bergamo, Italy—how they did it. Here are the pros and cons, what to expect, and how to set yourself up for success if you find yourself among the lucky full-time-remote workers and want to change up your scenery.
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Getting started, and deciding where to go
Not sure where to start? Andrea Valeria, a remote-work blogger who started her nomadic work style five years ago (in Buenos Aires before relocating to Mexico City) says that easing yourself into the transition is key. While it may be tempting to go all in and sign a year-long lease somewhere totally new and exciting, she advises building up to being a nomad year-round. “There’s a fine line between ‘this is the best thing ever’ and not having enough time to work, because there’s a lot of self discipline involved,” Valeria says. “To start, I would say take a few short [working] trips, maybe two weeks, near your home and see how it feels.” Learning how to strike a balance between working while traveling—this isn’t a vacation—while the stakes are lower (you’re not too far away; you haven’t left your lease) can help you find out if being a digital nomad is for you.
When you are ready to fully commit to life on the road, look for month-to-month accommodations for more flexibility. Websites like Airbnb, Vrbo, and Booking.com have long-term options (you may even get a discount if staying for a long period of time), though it’s also possible to work with local real estate agents for a short-term rental.
As for choosing a destination, Valeria recommends looking at cities that have a history of catering to remote workers. “There are places that are already popular for digital nomads and for good reason,” Valeria says. “They have what they need to work, to live affordably, to be safe, and there’s a community.” They are often places with more lenient visa processes, too; you might consider countries that have rolled out remote-work visas during the pandemic.
Don’t forget that, regardless of where you’re bedding down, you may still be expected to work nine to five in the timezone where your employer is based. Amber Edwards, an expat coach and founder of 30 Day Blaxit, a company that helps Black individuals move overseas, knows the feeling. Edwards previously worked in Qatar, where it was common for her to have to field phone calls at 11 p.m. in her local time zone, which was still the afternoon in the States. “Even though it’s tempting to explore the East, I would stay within a few time zones of your employer,” Edwards says. “It can be pretty rough otherwise.” Matt and Chelsea Gillespie, married digital marketing and design professionals who spent two years living in various cities in Europe with their then-toddler, usually had to start work their eight-hour work day at 2 p.m.
While getting a change of scenery every month worked for the Gillespies, staying in one place may be more appealing to others: Valeria says staying in one city helped her develop a good work routine, and made it easier to plan excursions that didn’t feel rushed. Finding that sweet spot might be important in avoiding burnout.
Actually getting work done
Think remote work is all jet setting and logging in from the beach? It's also about the work. Whitney Whitehouse, a photographer who lives and travels throughout the United States in her van with her dog, says one of the hardest parts of working from the road was simply putting in the hours. “For me, one of the biggest challenges is finding the discipline to actually sit down at the computer and work,” Whitehouse says. Chelsea Gillespie agrees: “You have to live like you’re not on vacation. You need to find your balance.”
The Gillespies and Whitehouse advise setting up or identifying a designated work space where you can switch into work mode. Chad Wyatt, Founder of Remote Jobs Co., says it’s important to set a schedule and boundaries. “If you need to work, use a co-working space or a private room,” he says. “Don’t work in a hostel, at the beach, at a bar, or anywhere around other people. It’s not the activities that tempt you, it’s the people that influence you to do things. If someone says to you, ‘Let’s go to the beach and have some beers,’ it would be hard to turn that down.”
Other considerations include access to Wi-Fi, remote-work blogger Valeria says. While a beachside bungalow may look idyllic, not being able to easily or steadily connect to work and team meetings can quickly become a nightmare scenario. It’s standard practice to ask your landlord what the internet speed is (you’ll need at least 1.5 megabits per second to meet web-conferencing demands, which can be challenging to achieve if others are using the same Wi-Fi). As an alternative you can seek out co-working spaces that guarantee good web connection, or purchase a personal Wi-Fi hotspot of your own.
Connecting with others
Many larger cities already have built-in remote work communities, and it’s just a matter of finding them. Edwards recommends searching Facebook for groups that have the destination and words like “traveler” or “expat” in the title (like “Expats in Costa Rica”). Often, these groups serve as good places to meet others and can get your questions about local life answered. There are also several general expat websites that can help, such as the Expat Network and International Citizens, which connect travelers and have a wealth of information about everything from obtaining visas to acquiring a local phone number.
Still, even with these information libraries, many remote workers find loneliness is one of the biggest challenges of life in a new place. Wyatt argues that you shouldn’t be afraid of trying to make friends the old fashioned way—there are many people in the same boat. “At first it will be daunting to just openly speak to a stranger, but you will realize that these strangers will most likely want to speak to someone, too,” Wyatt says. “If you are looking to make more lasting friends, I would say try out a local gym, take a class, go on an excursion, or do something where you are kind of forced to speak to people.”
The inevitable logistics
While working from anywhere may seem glamorous, there are myriad unsexy details to work out, including paying taxes, getting insurance, and having an emergency back-up plan in case of an accident, natural disaster, or, you know, a worldwide pandemic.
As a U.S. citizen working for a U.S. based-company, you are required to file taxes with the U.S. Internal Revenue Service (IRS), even if you’re living abroad. Depending on where you are and what type of visa you’re on, you may have to pay taxes to that country, too. Hiring an accountant who specializes in remote work (either outside your home state or abroad) can save you the headache of learning those tax laws yourself. “Get a tax professional to help you out with these things to make sure that you are doing them correctly, because it can get complicated quickly,” Valeria says. “The good thing now is that a lot of companies are hiring remote workers, so they may have the systems in place to set you up for correct taxes.”
Just like at home, you're likely to need insurance that helps pay for healthcare ranging from emergency room visits to medications. If you receive insurance through your employer, however, make sure to verify what it covers, and where; international coverage is typically limited, and deductibles and minimums higher. Even if you're healthy, it’s worth looking into travel-specific insurance providers, like WorldTrips or World Nomads, in case of surprise illness or injury. Preparing for the unexpected and having a back up is particularly important now, while there is still so much uncertainty surrounding international travel and the coronavirus pandemic. Wyatt recommends, at the very least, having money (or points) set aside that could cover a plane ticket home if absolutely necessary.
Enjoying your time
As far as Edwards is concerned, “it’s the perfect time” to work from anywhere. The pandemic has changed many aspects of everyday life, and one of the few positives is that it’s allowed new industries to dabble in remote work. Just a few years ago, most digital nomads were largely creatives of some kind, but going forward, location-independent workers could run the gamut from human resources professionals to engineers to educators.
While you may maintain the same job, there is a feeling of freedom when you’re not confined to one desk, one office, and one location. “That freedom and flexibility, to explore and experience a new culture and place, makes it all worth it,” Valeria says.
Originally Appeared on Condé Nast Traveler