How to Decide if Remote Work is for You

So you’ve been secretly coveting and silently salivating at all those bragging travelers who live and work abroad, and wondered how you could get a piece of the pie… Well, listen up!

If you’re curiosity has driven you to obsession and middle-of-the-night Google searches for working abroad or remotely, this article should give you more insight to make an informed decision or narrow down your options.

For people who have never traveled internationally, or don’t do it often, your first reaction might be trepidation and doubt, “How can I do this? It will cost too much. I don’t want to travel on my own.”

You Don’t Have to Do It Alone

About a few years ago, a program emerged with a novel concept: Get some people who love to travel and want to ditch the desk life to travel to countries around the world while they work for their jobs (or their own clients) remotely – i.e. away from “home.”

Honestly, I would’ve done it if I could. It was one of those too good to be true opportunities. The company was called Remote Year, and honestly it got plenty of bad press from some sour apples in the group. Complaints of the types of accommodations, lack of organization, and poor internet service were at the top of the list. Then there were complaints that were out of the company’s control, like social dynamics and the forming of cliques that lead to the exclusion of other participants.

“There are lots of remote travel programs popping up everywhere, which says that there is clearly a market for this business,” said Ebonee, a journalist from New York. “However, the main reason I feel some remote travel programs aren’t as successful as others is because they fail to make people feel like the remote travel experience is worth the high cost of the program.”

Well, a few bumps of such an innovative start-up didn’t stop them. In it’s third year, Remote Year continues to work out the kinks and keep people traveling the world while working.

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Peering out from a penthouse in the Poblado neighborhood in Medellin, Colombia.

Can I just add that 5 out of 5 of these companies had Medellin, Colombia as a destination. I’m in a hot spot, yall!


Now there are several other companies like it. Their description has been chiseled down to being “logistics companies.” They take care of the accommodations, all you’re flights between destinations – excluding the initial and final flights, work-share spaces, events and excursions, and guarantee wifi access, among other other perks, depending on the company. Below is a list of the ones I’ve discovered and a quick blurb on each, according to moi!

Remote Year  – Take a year off from your normal life to travel the world with 50 to 80 adventure-seekers, but keep your day job!

Remote Experience – Let me break it down for you. In case swallowing a whole year of traveling to random places is too much, you can opt for a month-to-month, four-month segments, or the whole dang kit and caboodle! They focus on one continent within a segment, visiting a different country each month.

Wifi Tribe – Over here, flexibility is key. This small tribe of 12 to 16 (and, occasionally, 25 at the most), wants you to buy in on your own time. Live your life’s travel chapter out all at once or spread the wanderlust over the 365 days time limit. You even buy your own flights. Did someone say glitch fare?

Unsettled – This happy and hip feel-good company that hosts work “retreats” hopes you love on one another, and is ready to let you live your life, internationally, on fleek.

My Wander Year – This black-owned and operated company is open to all creeds, nationalities and colors. It even opens its arms to traveling families, which means you can bring your bay-bay’s kids lovely children too! Picture it: Your son or daughter could be passport heavy before the age of 10.

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This could be you on an excursion… but you have to think about it.

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Things to ask yourself when deciding if this is something for you:

1. What do I want of this experience?

Are you looking for a way to parlay a vacation into a year of traveling? If so, you might want to look at cruises around the world. Most of these companies really are work + travel set-ups. If you are hoping to network, have your intentions and your actionable items together – don’t expect them to happen without concentrated effort. Also keep in mind, not everyone on these trips are their own bosses. To my surprise, many work for companies who said, “YES” to their year of wander.

2. How long do I want/can I afford to be away?

Doing an experience like this could be a shock to anyone’s system. You’re not just moving abroad to “A” country, you’re moving abroad to several countries throughout the year, so that’s culture shock, after culture shock, after culture shock. For those longer programs, you need to get your mind right! Don’t get stuck on comfort. Be malleable and ready switch gears.

3. Where do I want to go most?

You may not find a program that hits all your dream destinations, but if you have  what you want in mind, you’re more likely to narrow down the choices that best suit you.

4. How do I to operate my business remotely before I go?

Know the time differences of every country you’ll be in, and when. And if you’re traveling long-term, definitely mark Day Light’s Saving on your calendar! Know how you will make calls, determine if you’ll need to do video chats (and which program works best), set a work schedule and communicate that with your coworkers or clients.

5. What if I don’t like the people?

It happens. Whether you get bad batch of folks, or the best group of people who become your “tra-mily”, just know that you have options. Most of these experiences are set up so that you will have your own time with the option of fraternizing with those… “other people” on your trip. But go in with an open mind, and I’m sure you’ll be fine.

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Soaking up the local culture in Cambodia.

Saying yes to such an experience, will definitely be one you’ll never forget. Life is about exploring the unknown, fulfilling your dreams, and taking (calculated) risks that sets you at a higher vibration. If this is something you’ve always wanted to do…  Guess what, opportunity’s knocking!

But these programs don’t measure up for everyone. “[My friend and I ] were only with [Remote Experience] for one week when we decided to leave because we felt we could do it on our own for a fraction of the price,” Ebonee said. “We felt as though we were paying the founders to be our travel agents instead of having more of a remote family network where members of the group were more connected and shared more unique experiences together.”

However, Joelle, a TV producer from New York, recommends Wifi Tribe because of its convenience to travel for short or long-term throughout the year, and “still be a part of the tribe.” She added, “Just do what feels best to you without the full commitment. Again, I’m a freelancer. Commitment is not number one for me, but experience, quality, good vibes – I’m all about that.”

Still unsure? Watch this video of three professionals who participated in Remote Year, and get the real deal on what it was like to embark on a year’s journey with 74 strangers to 10 countries and 12 cities.

And if all of this still doesn’t impress you, you could always do it yourself… but take notes from these companies who seemed to have cooked up a recipe for world travel that works.

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