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How to Travel the World Without Quitting Your Job, According to People Who Did It

10 minute read

It’s a fantasy that crosses many of our minds at some point: Why don’t I quit my job and travel the world? While it’s a nice thought, the reality remains that in order to travel, you need money, and to have money, you need a job.

But thanks to the rise of remote work, it’s now very possible to work and travel at the same time. All you need is a device with access to the internet — and permission from your boss, or a reliable staple of clients if you’re a freelancer. People who do it might work for companies based in the U.S., but live in Europe, Asia or elsewhere. To get a better understanding of how to accomplish this balancing act, below, five remote workers share their advice on how to manage the best of both worlds.

Start with the right mindset

In addition to travel preparations, remote workers also spoke on the importance of preparing themselves. As Trevor Gerhardt, a programmer for a U.S.-based software consulting company who is currently in Bali, Indonesia, says: “Working remotely full time isn’t for everyone, just like living in New York City or Florida or the Midwest.”

But he adds that it doesn’t have to be an all-or-nothing endeavor. “For a lot people, one year or a few months of a work-travel program can be just the right amount of experimenting with the lifestyle. It will also bring them priceless experiences, deep friendships, and eye opening knowledge of the world.”

And Carolina Borrás, the director of customer education at online drawing tool Scribble Maps who is currently living in Cartagena, Colombia, says those deep friendships will prove incredibly valuable. “Simply going to a new country won’t change your life necessarily,” she says. “But by fostering close relationships with people who you mesh well with you can engage into a meaningful friendship with them.”

Trevor Gerhardt practicing a yoga pose on top of Toubkal, the tallest mountain in North Africa, located in MoroccoCourtesy of Trevor Gerhardt

Planning your travel

Undertaking a foreign adventure away from home can be daunting, but there are some steps you can take to prepare yourself.

In terms of accommodations, some suggest Airbnb and hostels for a balance of comfort and social interactions. “You can usually get quite a bit cheaper Airbnb apartments if you’re looking in four-week blocks. Sometimes it’s 50 percent off,” says Steve, a software developer for a Denver company who is currently living in Mexico City, who asked not to use his last name. He says it can be a good idea to ask Airbnb hosts in advance for a screenshot of an internet connection speed test, as quality Wi-Fi is crucial for remote work.

A hostel, he says, is “usually a really easy way to meet other people and there’s usually a few other people doing the same thing where they’re still working while they’re traveling.” He says that social media groups on Reddit and Facebook can also prove valuable for meeting like-minded individuals who are traveling.

Ask your boss for permission

You can plot every detail of your itinerary, but it won’t matter much if your boss won’t approve of you leaving the office — yet alone the country — to do remote work. People who have done it say the key is to give your manager little reason to say no.

“For me, it was a straightforward discussion about the logistics for work and whether or not it was something I should do personally,” Gerhardt says. “I had already spent significant time working from home and working around the states on various trips. There wasn’t an issue of accountability to be worried about.”

And if there’s any concern or hesitation from your boss, Borrás suggests you ask for what she calls a “trial period.”

“Even a monthly period where you work from home on your laptop just to ease the management into knowing that they can trust you to deliver the work,” she says. “Because that’s the biggest issue, right? Your management team has to trust that you can deliver work at the time that is required.”

Carolina Borrás standing in front of the Angkor Wat temple in CambodiaCourtesy of Carolina Borrás

Surviving as a freelancer

Others with dreams of a remote career may consider quitting their full-time jobs to go freelance — if they hadn’t already done that already. While freelancing can afford people the freedom to work and travel on their own terms, it can be a huge risk if steady income dries up.

For Katherine Conaway, a writer, consultant and producer who is currently based in Medellín, Colombia, freelancing is simply a way to guide her journey while she works abroad.

“I came into it with a relatively low number of hours, but I also wasn’t expecting to make any money, so then I just started building out my travel and my life around the income that was coming in,” Conaway says. “If I’m on a certain budget, that dictates maybe what country and region of the world I’m in. It dictates the kind of accommodations I stay at, and the way I spend my money. But that’s the benefit, my life is always flexible to meet whatever income level I’m at for that chunk of time.”

Conaway’s advice? The age old practice of networking. “It sounds lame and I used to think, ‘What does that even mean?’ For me, it means I’m always open for new work,” she says. “I’m always talking to people about what they do, sharing whatever I’m actively doing.”

Katherine Conaway at a falconry tour in the desert outside of DubaiCourtesy of Katherine Conaway

Balance work with sightseeing

Unlike most tourists on vacation, remote workers still have responsibilities — so how do you manage to stay focused on work when you’re surrounded by so many new people and experiences just waiting to be discovered? It requires some self-discipline and an efficient use of time, remote workers say.

“My number one priority is my income, because without my income, I can’t travel,” Borrás says. “If I have that as my priority I also have a set of travel priorities.”

She says when she was living in Mexico with a group of friends, she managed to maintain high productivity by working during the week while scheduling restaurant trips for the evenings and small trips for the weekends. “That is really the way that you balance it,” she says. “You have to acknowledge that you’re not going to see everything that you want to see, and you have to be okay with that.”

Another option? Schedule small bursts of productivity if possible to maximize time for sightseeing.

“Find a way to condense all the time that you normally waste throughout the day working into a shorter period of time so that you’re forced to do all your work in a small, productive window,” Christopher Schwab, who owns and runs Washington, D.C.-based cleaning service Think Maids while living in Tokyo. “You may do all your productive work in two hours a day or four hours a day instead of eight, so that you have the rest of the day to actually do what you want.”

Christopher Schwab with a monkey while en route to a mountain temple in MalaysiaCourtesy of Christopher Schwab

How to deal with time differences

For remote workers who choose to live in countries in distant time zones, maintaining a normal work schedule can be challenging. As your company or client may be starting their day, you might be on the verge of falling asleep — and vice versa. People who have done remote work while traveling say that developing a routine can be one of the most important steps to maintaining communication across time zones.

“It’s maybe a little of a boring answer, but a very effective one: You have to have a to-do list,” says Schwab. “It’s very easy when you’re in a different time zone to screw things up or screw appointments up or forget things, so it’s super important to have a schedule or to-do list and some sort of process throughout the day that you follow.”

It’s also helpful to have a place that you can always count on for spur-of-the moment work, says Steve. “The most important thing is to have a space that you know is going to be available and quiet 24 hours a day,” he says. “Having good internet has been the biggest challenge, so I’ve been gravitating to places with co-working spaces because they’re pretty reliable.”

Should you join a remote-work program or go at it alone?

A number of programs that facilitate the process of remote work for travelers have emerged in recent years. These programs handle the logistics by booking flights, accommodations and workspaces for attendees over a period usually ranging from one month to a year. In addition, staff members often lead groups and curate activities to develop a sense of community for those working in foreign countries.

Perhaps the most well-known of these programs is Remote Year, which sends dozens of people on group trips to new countries every month for either four months or a full year. Prospective group members build a profile with information about themselves. If approved by Remote Year, which says it works to assemble groups with diverse backgrounds, industries, and countries, the program will match you to your preferred itinerary. The 12-month program costs $27,000 total with a down payment of $5,000 and $2,000 monthly payments; the four-month program costs $11,000 total with a down payment of $3,000 and $2000 monthly payments as well.

“If you’ve never worked and traveled at the same time — not just answering emails, but putting in full, intentional work days — and can afford the price tag, then it’s the perfect way to get started,” says Gerhardt, who traveled via Remote Year in its first year of operation from June 2015 to May 2016. Beyond the pre-planned accommodations, he says it’s beneficial to be around “50-plus other explorers that will help [you] meet exponentially more people” and “get the down low on what’s happening when you’re in a city,” but also being around others who also need to work so that you’re not constantly distracted.

Conaway, who traveled via Remote Year in its second group from February 2016 to January 2017, says the program can be great for people who want an entry into working abroad, “but I also feel like sometimes, though, people struggle the most because they expect Remote Year to be perfect and to take care of everything.”

“If you’ve never traveled or lived abroad and you’ve never dealt with the inherent discomfort of that experience and the fact that things are going to go wrong, and you’re going to get sick, and you’re going to miss home… you’re going to have a hard time,” she says. “So if you come and expect Remote Year to be perfect and the company to be able to do everything to make it perfect for you, you are going to be disappointed, so you have to have a reasonable expectation for what they can do and for what it means to travel to a different place every month for a year.”

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