A Beginner's Guide to Remote Work - Condé Nast Traveler

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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.

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A Beginner's Guide to Remote Work - Condé Nast Traveler
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