How to Use a Flea Market to Make a Living While Traveling (and Other Tricks for the Working Vacation)

How to Make a Living While Traveling
by Sarah Landrum
December 28, 2016
Careers and time off aren't mutually exclusive. Sometimes, working on the go is actually the best move you can make. Here's how to nail the working vacation.
There’s something liberating about discovering new parts of yourself and the world at the same time. People, places, food, experiences. You’d love to do more of it. The only things holding you back? Extra time and money.

When the end of your last vacation arrived, you probably dreaded the return to the office, stressful meetings, and the sharp scream of your alarm every morning. Maybe you wondered: “What if I just don’t go back?” But then you probably brushed it off.

On initial consideration, it seems impossible to make a decent living while gallivanting around the globe. You plan your trips according to vacation days, not work weeks. But whether you’re looking to try for your first extended holiday or to transition into a full-time mobile and nomadic lifestyle —completely free of the office grind—the problem of finding money on the move comes with more solutions than you’d think.


The beauty of living in an internet-loving world is that working remotely isn’t unheard of. In fact, it’s fairly common and, for some companies, actually welcomed.

As long as you’ve got an internet connection, you’re in business. There are many freelancing sites out there that you can use to pick up paid gigs regardless of zip code. Taking on contract work will help you build your portfolio while you’re gone and provide you with some ways to explain the “work gap” you’re knowingly creating in future interviews.

Use Your Native Tongue

If you’re reading this, there’s a high chance you’re a native English speaker. Translation and editing skills are in high demand in many countries, and the assignments can be very lucrative. Teaching English, too, can be a great gig if you know you’ll be staying in one place for awhile.  

The key is to utilize any and all of the skills in your arsenal rather than thinking specifically in terms of your resume and past experience. From teaching languages to babysitting services to setting up simple websites for budget hostels and hotels, get creative with that entrepreneurial brain of yours.


Maybe you’ve postponed your long-term escape because you’re worried about leaving your home for an extended period of time. You’ve worked really hard to find a place you love and call your own—and you don’t want to lose it.

But having the burden of paying rent while you’re gone (and the pain of knowing you’re paying for a space you’re not even using) will definitely limit your travels.

Look into finding a long-term subletter. This should be someone you can meet and build a relationship with before leaving so you can trust them with your space while you’re away. Ask friends if they know of anyone who might need a place to stay in the coming months. You’ll cover part or all of your expenses and get some peace of mind.
Ask friends if they know of anyone who might need a place to stay in the coming months. You’ll cover part or all of your expenses and get some peace of mind.
On the other hand, if you don’t mind different tenants, look into renting your space on Airbnb. For some, this can turn into a lucrative side hustle, sometimes bringing in hundreds to thousands of dollars. If you travel on the cheap, you might actually cover your expenses and turn a profit.  

When you consider either route, the best way to get started is to talk to someone you know who’s already familiar with the subletting process. Chances are you have an acquaintance who has been Airbnbing their place. Take them out for a cup of coffee. Other good rules of thumb: make sure you have someone who can take care of emergencies while you’re gone and that you outline some clear house rules (so you won’t get long-distance calls from angry neighbors or property managers about late night parties).

GET THRIFTY on a working holiday 

If you’re considering a big career move and looking for a permanent travel solution, you’ll most likely want to eliminate excess expenses and belongings from your life. By selling off the things you won’t need while mobile—a car, furniture, and bikes, for example—you can actually make some extra money to add to your travel fund. Remember, all these items are replaceable.

Also, work on downsizing expenses. You won’t need car insurance, a gym membership, or Netflix if you’re constantly plane-hopping. You can save a significant amount of money for your travel nest egg by eliminating these costs.
You won’t need car insurance, a gym membership, or Netflix if you’re constantly plane-hopping.


Travel writing and blogging on the working vacation are also great solutions for making a living on the road. It’s a competitive market that fluctuates often, but if you have the determination to make it work, you can find resources out there to help you along the way.

If you’re going to be heading to strange or uncommon destinations, try pitching some magazines or blogs on writing about your experiences before you go. The pay’s usually not great, but everything counts. Plus, you’re building your portfolio.  

...OR SELL your discoveries 

If you are a traveler that prefers cultural immersion to the average tourist experience, capitalize on that passion. Look into becoming a tour guide wherever you’re posted. You’ll not only put some extra money in your pocket, you’ll learn about the city as well.

If you have an entrepreneurial spirit, now might be the time to start an Etsy or Ebay shop. You can hunt through local markets to find unique cultural pieces that you can resell to American audiences. Kilim pillowcases can be quite the money-maker.
You can hunt through local markets to find unique cultural pieces that you can resell to American audiences. 
The only challenge is knowing what to look for. You’ll have to study up on the value of certain items before purchasing. One way to do your research is to search the names of cities or countries in Ebay or Etsy to see what others are selling. This way, you’ll know what will make you some cash and what won’t.

All of the options listed above take hard work and dedication. No traveling entrepreneur will claim that making a living while globetrotting is easy or the most secure way of supporting yourself, but it can be done—and it’s worth it.

Do your homework, make a plan, and stick to making it happen. Anything is possible with drive and a bit of hard work.

Have you ever traveled long-term? What were some ways you made it work?