10 Unexpectedly Cool Ways to Fund Your Travels Forever

Couple exploring Greece off road and enjoying some epic sunsets – The Ultimate 2-Week Greece Road Trip Itinerary

If you are looking for ways to fund your travels forever, these 10 unusual, but unexpectedly cool jobs are waiting for you.

A two-week vacation is nice. But if you’ve caught the travel bug, odds are you want more.

You want a way to earn money on the road so you can travel long-term — for months, even years, at a time.

You’ve probably already heard of digital nomads who support their travels by teaching English, freelance writing, running e-commerce stores, or becoming fancy travel “influencers”.

But what if none of these traditional travel-friendly jobs sound interesting to you?

Turns out, you’ve got options. There are loads of ways to earn money while traveling, many of which you may have never heard of.

Here are 10 unusual and genius jobs you can use to fund your travels forever. 

10 Unusual Ways to Earn Money on the Road

1. Traveling Personal Shopper

If you love shopping, this one’s for you. Working as a traveling personal shopper can take many forms. But to give you an example, my wife’s friend-of-a-friend earns a cushy living traveling between Colombia and the United States buying luxury goods for rich Colombians.

Gucci purses, Rolex watches, exotic Asian poodles…you name it.

In Colombia — as with many other countries in the world — it’s hard to get your hands on such rare luxury items. And most people don’t have the time to jet-set to a different country whenever they want a new outfit.

To earn money this way, you obviously have to have some powerful connections willing to pay handsomely for convenience and safe delivery. But even without rich connections, there’s another way you can make money shopping abroad…

2. Seasonal Activity Instructor

If you love outdoor activities, you can support your travel lifestyle by teaching them to others.

For example, I met two guys who worked as ski instructors during the winter ski season and surf instructors during the non-ski season alas summer. After each contract, they’d take a couple of months’ break to travel around full-time in their skoolie (that’s what the cool kids call a custom-built school bus if you’re wondering). 

They get paid to do what they love every day, and they have the freedom to move around to new locations each season. 

If skiing and surfing isn’t your forte, there are tons of other skills you can teach — from scuba diving to rafting to parasailing.

With activities like scuba diving, you don’t even have to worry about the season. Just bounce around from island to island whenever you need a change of scenery.

This type of work requires you to live in each location for several months at a time. This gives you a chance to build stronger relationships and immerse yourself in the local culture. 

3. Non-Seasonal Instructor

If seasonal outdoor sports aren’t your thing, you can still use your talents to make money traveling.

For example, when living in Chiang Mai, I met a couple who supported their lifestyle by offering salsa dancing workshops in every city they travel to.

Or if you’re into yoga, there’s plenty of yoga-focused communities around the world (also in Europe!) where you could find work — whether that be in hostels or actual yoga studios.

Just remember with any of these types of in-person jobs, you should have a visa permitting you to work. 

There are plenty of instructors who work informally while traveling abroad, but this is technically illegal. If you can’t secure a work visa, another option is to trade your time for free food and accommodation. If you aren’t getting paid directly, you’re considered more of a volunteer, and the work visa is less of an issue.

4. Importer and Exporter

In its simplest form, importing and exporting is just buying something cheap in one location, then marking up the price and selling it somewhere else. 

For example, we met a Colombian traveler who exported name-brand socks from China and sold them in Colombia. 

Unfortunately, if you want to build a legit, large-scale operation (which isn’t a bad business idea), you have to jump through a bunch of legal hoops. 

But you can also earn a decent income with an under-the-radar business. Now, I’m not encouraging anything illegal here — you have to research the laws in the country you plan to sell in — but the opportunity is ripe.

In fact, one time we even used this business method to pay for one of our trips. In many countries, name-brand electronics like Apple cost a fortune compared to the U.S. 

So if you were to hypothetically pick up a couple of Macbooks before flying out, you could potentially resell them for several hundred dollars profit each. Hypothetically. (wink, wink)

Add in a couple of iPhone flips, and you’ve just paid for your entire trip.

In many places, Customs limit the amount of new merchandise you can bring into the country. That means you e need to choose items with the highest potential margins. You might also want to lock in your buyers and collect deposits before spending your money, so you don’t get stuck with a bunch of products.

In addition to electronics, you might also consider unique handmade items that are easy to mark up. I know of another traveler who filled a suitcase with Alpaca sweaters from Peru. He then resold each one in New Zealand for over $100 profit each.

5. Internet Scopist

Internet scoping is an under-the-radar job perfect for travelers. It’s also tricky to explain.

Basically, in legal court proceedings, a stenographer uses a stenography machine to capture everything that is said. This machine has its own special shorthand language. And since the stenographer is typing a mile a minute to keep up with the conversation, the final report is littered with errors.

An internet scopist is a freelancer who takes these error-ridden drafts, compares them to the audio recording, and creates a final transcript of the proceeding.  

To become a scopist for court reporters, you need to learn basic legal terminology and how the stenography language works. There are several online certification programs that can get you up and running as quickly as possible. 

Since these programs are basically training you in a new career, they require a decent investment — usually a couple of thousand dollars.

Due to the higher bar to entry, it’s not for someone who just wants to make a quick buck to fund their travels for a few months. Rather, it’s a location-independent career for people interested in law who are in it for the long haul. 

6. Feet Pic Seller

This guide isn’t called “unusual ways” to fund your travels for nothing. As weird as selling pictures of your feet sounds, I’ve actually met travelers who do it to support their adventures.

During the thick of the pandemic, we got trapped on an island in Cambodia for three months with a handful of other travelers. As time passed, savings dwindled.

We kept our income alive by freelance writing. Other travelers volunteered at hotels and hostels in exchange for accommodation. And a couple of clever girls got creative and figured out how to sell feet pics online for cash. 

They told us that while it had the potential to get weird, it didn’t have to. 

Yes, many buyers are foot lovers who ask you to do weird poses with your feet. But you can also make money selling pictures to stock photo sites, modeling agencies, publishers, and foot-related companies who need images. 

In the end, you never have to do anything you’re not comfortable with. 

If you have pretty feet, want to travel indefinitely, and don’t have another income source — it could be the perfect solution. 

7. Drop Servicer

You’ve probably heard of drop shipping — an e-commerce model where you essentially act as the middleman between buyers and suppliers, eliminating the need to hold inventory.

The drop servicing business model is similar, just with digital services. It’s basically the same thing as an agency, except instead of hiring employees, you use a team of freelancers.

Think of it as freelancing on steroids. When you’re a freelancer, your income is tied to the number of projects you can cram into a day. But if you outsource all your projects, that income cap vanishes, and your main objective becomes landing as many deals as possible (and managing your team). 

With drop servicing, you don’t necessarily need to be an expert in the service you offer, but it helps. And while it’s possible to build a successful business with any type of service that businesses need, some offers are easier than others.

An ongoing service with high perceived value — like email copywriting, for example — would be easier to scale than offering one-off logo designs.

With logo design, you’d need to land tons of clients each month to sustain your income. With an ongoing, high-value service, you could coast after landing a handful of long-term clients.

8. Tree Planter

While hiking a volcano in Nicaragua, I met a young couple with a fascinating travel lifestyle

For a few months per year, they planted trees like crazy in Canada. Then for the rest of the year, they traveled full-time, living off their tree-planting earnings.

Tree planting season usually lasts a couple of months in Canada depending on your location. Planters are paid by the tree. So the faster you plant, the more you earn.

And if you’re fast, you can earn a ton.

At one tree planting company, A+G Reforestation, the top three fastest planters averaged $526 per day. The average season lasts around 55 days, so that’s $28,930 in less than two months. And since you sleep in tents and food is provided on workdays, most of your earnings go straight to your travel fund.

Now, you can’t expect to be one of the three fastest planters as a beginner. In fact, you’ll most likely earn half as much while learning the ropes. But it’s still an interesting opportunity. 

It’s also brutal. Sleeping in a tent for months at a time has nothing to do with glamping, and planting trees all day isn’t the most comfortable job either. It’s physically demanding and takes a toll on your body. But I guess that’s why you get paid the big bucks.

9. Video Game Streamer

If you would’ve told me 15 years ago that I could make a great living playing video games, I wouldn’t have believed you.

But today, not only can you make a full-time income, but you can do it from anywhere in the world. 

Twitch is the most popular platform gamers use to earn money. You start by creating a channel to live stream games. If you build a decent following, you can earn through subscriptions, ads, donations, affiliate commissions, and more.

Working as a traveling gamer requires a different type of travel. Since you need to lug around and set up a bunch of equipment, you probably won’t be hopping around from hostel to hostel with a light backpack.

Instead, you’d focus more on longer stays in private accommodation where you can set up shop and game comfortably.  

10. Traveling Chef

If you can whip up delicious food, you can get a job almost anywhere.

You can work in seasonal resorts, cruise ships, summer camps, normal restaurants, or even land private chef gigs for rich yacht owners.

If you’re looking for something less formal, you can also find places willing to trade free accommodation for your cooking skills almost anywhere in the world. 

Now, it’ll be tough to land higher-level jobs without formal training or experience (no matter how good your signature PB&Js taste). This training usually comes in the form of an apprenticeship or culinary degree, depending on the country you’re from. 

In most cases, that means working as a chef is more of a lifelong career than a way to earn quick cash on the road. That said, if you know your way around the kitchen and are willing to work for accommodation, you can find opportunities that don’t require formal training.

Wrapping Up

You don’t have to follow the crowd.

Just because your Instagram feed is littered with bougie travel influencers doesn’t mean that’s the only way to sustain full-time travel.

As you can see, all you need is a bit of creativity and determination to build your dream travel lifestyle. 

No matter what your skills and interests, there is a travel job for you.

You just need to find it.

Mitchel Glass is your typical nomadic backpacker. Or at least, he was. But after stopping in Colombia to take “one week” of salsa lessons, his life took a sharp left turn. He met a cute Colombian girl in dance class, fell in love, and got married. Over half a decade has passed since he left his career to travel the world as a digital nomad, and he’s never looked back.