How to Make a Living While on the Road

Attention aspiring travel bloggers and adventurers! If you're ready to see the world, here's our guide to making a living while on the road.
Yellow Volkswagen Westfalia or Kombi van driving through the desert

It’s every wanderluster’s dream: hop from place to place, experience new cultures, and befriend friendly locals—all while getting paid. And as fantastical as it may sound, it’s actually possible to work while you’re on the road. In fact, at this very moment, many people are doing just that all around the globe—so why can’t you be one of them?

Find your (portable) passion

Adventure journalist Jayme Moye loathes headlines like “How I Quit My Job to Pursue My Passion” — yet, in a way, that’s exactly what she did when she bid adieu to a secure tech job and leaped into the unstable world of freelance writing.

Working on the road isn’t all fun and games—but if you can make it work, it’s a pretty sweet gig. The challenge? You’ll only earn a living if you’re actually decent at whatever it is that you’re trying to freelance in.

You need a marketable skill—something that you’re good at, that companies are willing to pay for, and that will allow you to live the nomadic lifestyle you long for. We call this your “portable passion” because, ideally, it’s something that you also care a lot about.

There’s no need to go on a deep, soul-searching journey to find your portable passion; just think about things you already like to do. Have you been writing short stories for as long as you can remember? Do you have a knack for finding typos in brochures and on posters? Do random followers praise the photos you take as a hobby on your Instagram? Have you been making films since you were old enough to work a camera?

If you don’t have a portable passion, no sweat—there are other ways to find jobs that will allow you to travel.

Turn your life into a permanent vacation…sort of

The world is full of incredible places, but there are some destinations that truly thrive on tourism: think tropical resorts, mountain towns, and meccas for mega yachts. The one thing these places all have in common is that they’re almost always hiring personable people with exceptional customer service skills. While other people are paying to go on vacation, you’ll actually get paid to be there.

Of course, there are a few caveats: Life’s not always a vacation when you have to deal with jet-lagged tourists with unreasonable expectations, and you probably won’t make major bank in these types of roles. Still, if you like working with people and know how to make the most of your down time, this is a great way to fund an incredible adventure. And more than one person has turned a seasonal job into a full-on career in hospitality.

Consider realistic gigs that involve travel

International photographer and travel guidebook author are two great jobs that allow you to travel…and they’re also virtually impossible to get without some serious expertise. But your education and skills might offer other opportunities to travel with work. For instance, if you have a background in HR, maybe you can find a recruiting role that allows you to visit new places to find new hires. If your background is retail, seek a consulting gig that allows you to help new locations with their openings. Shift your thinking and try to identify different ways that you can apply your existing talents.

Be open to new experiences

There’s a lot to be said for keeping an open mind. If you’re hardworking and willing to try something new, you could end up in some supremely cool places learning completely new skills—think teaching English in South Korea, fruit picking in Australia, or working on a sailboat in the middle of the sea.

Identify your niche

Zim Ugochukwu had a thirst for travel and adventure and she was able to convert this into a business opportunity by identifying a gap in existing travel blogs and Instagram feeds. Her website, Travel Noire, is a publishing platform and communication hub geared toward travelers of color. These days, she gets paid to travel several times a month.

Maybe you, like Zim, have noticed a need that isn’t quite being served by what’s already out there. If you have an entrepreneurial spirit and an incredible work ethic, you could be on the cusp of the next great travel site/tour guide operation/consulting business/you-get-the-idea.

Get inspired

Maybe you’re lucky enough to know a professional traveler in real life. Outdoor adventure writer, editor, and filmmaker Hilary Oliver had one such person in her life: Her partner, Brendan, had a few years of freelancing under his belt when she decided to try her hand at the freelance life, too.

If you know someone who is already living the paid, nomadic lifestyle, shoot them a message or give them a call and ask if you can pick their brain. They probably have a lot of practical advice to offer that you can apply to your own quest to work on the road. Plus, they’ll be able to offer a balanced view of what life as a paid traveler is really like (hint: There’s more to it than what you usually see on social media). Ask around and learn how other people do it to get new ideas on how you, too, can make a living while you’re on the road.

Disclaimer: Hey! Welcome to our disclaimer. Here’s what you need to know to safely consume this blog post: Any outbound links in this post will take you away from Simple.com, to external sites in the wilds of the internet; neither Simple nor our partner banks, The Bancorp Bank and BBVA Compass, endorse any linked-to websites; and we didn’t pay/barter with/bribe anyone to appear in this post. Jamie Moye, Zim Ugochukwu, Hilary Oliver, and Brendan Oliver are not Simple customers. For more information about the terms and conditions of account ownership, please see our Account Agreement. And as much as we wish we could control the cost of things, any prices in this article are just estimates. Actual prices are up to retailers, manufacturers, and other people who’ve been granted magical powers over digits and dollar signs.