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How to Earn Money While Traveling: Fact and Fiction

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Want to make money while on the road? It’s definitely possible, and more and more people are doing it all the time—but you may need to change your thinking to make it happen.

Our first Unconventional Guide of 2015 launches this Tuesday morning. It’s all about what works—and what doesn’t—when it comes to heading out into the world as a long-term (or at least frequent) traveler.

The premise might surprise you: On its own, traveling has little to do with earning money. You earn money by making or sharing something that other people find valuable. That’s it. If you’re going to get paid while abroad, you have to think about what you can do that’s relevant and interesting to others.

What can that be?

Let’s first consider the most common things people think of when they think of “getting paid to travel.” As we’ll see, they’re all problematic in some way.

“Be a travel writer” –


This career has almost become extinct. Yes, there are some travel writers who are able to pay the rent or hotel bills, and a few that do particularly well. But these people are the exceptions.

In the age of Instagram, everyone is a travel writer simply by virtue of possessing a smartphone. Combine this fact with the changing world of journalism, where plum assignments are hard to come by, and you have a long road ahead if you want to be a traditional travel writer.

Companies may fly you around and put you up, sure. It can be nice in the beginning, and there’s nothing wrong with a free trip. But if your goal is to earn money (the subject of this blog post, as well as the new guide), it’s not the best bet.

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“Teach English in Asia” –


OK, this can work. Teaching is a great way to experience a culture in an in-depth manner, while making friendships and supporting yourself. There’s nothing wrong with that—in fact it’s highly positive—but it’s hardly “making money.”

You shouldn’t be an English teacher to make money, because you won’t usually make much. So for the purposes of this article, let’s say that teaching English in Asia is a great life experience, but not the best way to get paid.

“Buy things in one place, sell them in another” –


This is how I got started in business many years ago. I bought and sold items from around the world, ranging from coffee to LEGO sets to cigars and anything else I can find (no drugs, in case you were wondering—I didn’t have a good supplier).

“Buying and selling random stuff” can still work, but it’s increasingly harder due to globalization. These days, there isn’t much advantage to being “on location” anywhere.

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You can buy and sell stuff from the corner of your dorm room or home office. So what’s the point of doing it from afar when a dozen other people can do the same thing without getting a passport stamp?

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The strategies listed above are the most common approaches people take when they think about “working from anywhere.” But these strategies are rarely the best ones.

Here’s what I think is better: Build a career (or at least a side business) that is independent of geography. Establish a real business (first) or develop a marketable skill (first) and then take your show on the road.


Focus your efforts on finding a way to make something valuable—wherever it relates to traveling or not.

Cultivate skills that are relevant to the global marketplace, not just a desk job in one location.

Choose to actively learn however you can.

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Lastly, there’s one more big option. You can simply decide to not worry about it for a while, and build up a savings reserve before you leave to pay the bills that come up along the way. If you’re able to save up enough to travel, choosing to focus on the work transition a bit later, that’s also great.

Hailing from Canada—but now truly a global citizen—Nora Dunn has done all of these things, and she’s done them all very well. Originally a financial planner with a successful practice, Nora first hit the road with very little income at all, relying on savings. It didn’t take long for her to create a series of new careers—and now she’s been traveling full-time for nearly a decade.

Nora is the author of the Working on the Road, our new project which comes out less than 36 hours from now. With the right career, business, or side-hustle project, you’ll have far more options than if you simply head out and hope for the best.

Don’t be misled: You can travel and you can earn money while you are traveling. But the two things aren’t necessarily connected at the hip. In many cases, if your goal is to make enough money to support your adventures, you should spend real time thinking about it before heading out the front door.

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Working on the Road: The Unconventional Guide to Full-Time Freedom will debut on Tuesday morning at 9am PST / 12pm EST. This guide has been in the works for more than 18 months (!), and we’re excited to share it with you… very soon.

Images: 1, 2, 3, 4, 5

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