Freelancing While Traveling: How I Paid My Way for a Year

Freelancing While Traveling

Greetings from a Greyhound bus heading westbound towards Chicago. For more than a year now, I’ve been freelancing while traveling. I’ve been to more than 16 countries, including Europe, UK, Scandinavia, Mexico, Canada, and across the United States, getting by while writing for clients. It’s a great lifestyle and it sure beats punching the clock while being underpaid. Being able to see the world is a pleasure that 9-to-5ers only dream about—one of the reasons why I became a freelancer in the first place.

Freelancing while traveling isn’t as easy as it looks. Here are some insights that I’d like to share to you about how I paid my way for these last few years.

Before Leaping

If you don’t have a functional freelance business before hitting the road, you may face extreme difficulties while hitting the road. Finding time to write is going to be difficult, and the window of opportunity to get work done isn’t going to be as wide as a stationary lifestyle.

Keeping your work organized and backed up should be among your highest priorities. There’s nothing worse than losing an entire assignment or missing a deadline when you don’t have the “infrastructure” to absorb these possibilities.

How I can put this bluntly? Before leaping into freelancing while traveling, have your shit together.

Protect Your Gear

Getting my laptop stolen in Kreuzberg (Berlin) definitely set me back. In a scramble to get my gear back to a functional level, I visited a cheap place in the Sternschanze (Hamburg) that builds refurbished laptops. Luckily, I had the money and got my life back on track. Without this “emergency fund,” I’d have to scramble to find employment. Quite a challenge in a place where I don’t speak the native language.

Time Matters

As a traveling freelancer, my clients aren’t all based in my time zone. When traveling, you’ll frequently have to change your schedule around your clients—or make them aware that there’s an offset between your schedule. Working with US-based clients while hanging out in Glasgow? You’re going to have to factor in 5+ hours if the client is based on the East Coast. Their 9 – 5 is becomes my 2 – 10pm. For clients on the West Coast, that looks like 7pm – 3am!

Similarly, working with international clients while living in the US provides its own challenges. For instance, Australia is 16 hours ahead of EST. Making sure you and your client are on the same page can be a significant challenge.

Making Work a Priority

This might seem like a no-brainer to freelancers, but your work takes a higher priority when you’re relying on it for food and shelter! You’ll find that it can be hard to find a place to concentrate 100% fully on the task at hand, especially if your wi-fi source is from a public place (i.e. library, airport).

I can admit that this was a challenge when there was a party going around me. When I went to Mardi Gras last year, trying to get work done in The India House, a youth hostel not far away from Bourbon Street, was damn near impossible. I eventually had to seclude myself in a Starbucks to knock out assignments, jamming headphones into my ears to avoid the tantalizing bonafide Cajun sounds. Talk about FOMO!

Fringe Benefits of Freelancing While Traveling

When you are a foreign traveler, it seems that everyone is keen to roll out the red carpet as a way of measuring their own vanity. As a writer, it inspired many possibilities for queries and article ideas.

While writing and playing music in the Parisian neighborhood of Belleville, my host invited me to something called “contact improvisation”. A blend of modern dance and new-age inclusiveness, I found myself among a new realm of possibilities while a man hoisted a female playing violin over her shoulder.

Developing the Travel Mindset

Freelancing while traveling will eventually demand that you develop a travel mindset. Your mind will weigh how easy it will be for you to take on new clients, work on existing projects, and find the time to explore your new surroundings. Improvisation will steer your decision, especially when you have flight delays or buses stranded in the middle-of-nowhere.

In other words, you’ll learn how to roll with the punches. Freelancing is never routine.

Making Plans

“Failure to prepare is preparation for failure.”

That’s the rule of the road. Often, people think of it as a carefree experience that’s full of novelty. If you plan to work and support yourself, you’ll need to be acutely aware of your expenses and earnings. Your quality of life is directly dependent on your money saved and your work ethic. It may nice to relax by the lake for a week, but will your clients feel the same when their projects are left dangling?


If you’re planning on freelancing while traveling, remember that the cheapest way to live and eat is by acting like a local. The sooner you can acclimate to this, the sooner that you can create a budget that fits your life. Checking out the mountains outside of Krakow might be fun, but it’s certainly more worry-free when you realize you have the day off the following day to recover.

Eating like a local will balance your budget. In Europe, you’ll find food to be cheaper than the United States—especially for the quality. Your food budget will certainly change and you’ll find yourself deciding between the cheaper version of American food, or the local specialties from the local bakery that seems to only include locals.

Availability of WiFi

Your source of wireless internet will be your lifeline to maintaining a successful life on the road. WIFI becomes important to your workflow, and you’ll find yourself spending a long time in cafés or internet cafés soaking up the sweet, sweet signals. Without a consistent signal, you’re out of luck. You’ll quickly realize that your access to the internet is a high-priority.

As a general rule of the road, if you need wi-fi, go to McDonalds. They always have a good wi-fi connection.

Diversifying Your Sources of Income

As a freelancer, I’m always looking for new sources of income.

For me, I realized that traveling opened up more opportunities than just writing. For instance, I supplemented my income by busking, which provided so much writing material that I wrote a book on my experiences called The Guide to Busking.

Busking opened up a more diverse way of interacting with people. After all, sitting behind a computer screen can be isolating. What better way to meet that locals despite language barriers than speaking the universal language that is music? I can remember meaningful “conversations” with gypsies in Strasbourg, or arguments in Stuttgart with the street folk there. In other words, they provided a break from writing, but also material for future articles and projects.

Ultimately, I landed an interview from Squat the Planet, an internet forum for low-budget travelers, grifters, and outsiders. Since the interview, I’ve seen the sales of my ebooks go up, as well as my job opportunities increase. Clients often ask how experience I am at advertising my work, and it is no easier than giving them links to my interviews. If I can make money for myself, my clients feel that I can do the same for them.

Of course, this only scratches the surface of what makes freelancing while traveling so appealing (or daunting). It certainly is a lifestyle that is attainable, but requires a rational mindset that can anticipate all of the hiccups along the way.

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