Want to quit work and travel for years at a time? It is possible. Just ask Marco Ilagan and Francina Cassaniti. They quit work five years ago. They’ve been traveling the world ever since. And they have no plans, nor economic reasons, to ever return to a 9-to-5 lifestyle.

“I wanted to see the world — experience all that the world has to offer,” says Ilagan. “I have never been healthier and feel like I’m becoming the best version of myself.”

Added Cassaniti: “We are more active. We are meditating. We are connecting more with nature. And we are learning so much through traveling.”

Quit work and travel

There are just two things you need to do to make it work:

  • Cut expenses
  • And find a few smart side hustles — those that have few constraints on where and when you do them — to pay the bills that remain.

Cut expenses

While cutting costs dramatically seems difficult, it’s actually pretty simple. Ilagan and Cassaniti do two things to eliminate most of their big expenses: They housesit and travel-hack.

Travel hacking mainly involves using their stellar credit ratings to get credit card airline miles. Ilagan spends a few hours every month or two checking out what credit card companies offer the best bonuses for signing up. They get the cards; follow the rules; then use those bonuses to buy free airline tickets to the next place they want to visit.

But the biggest savings came from signing up with a housesitting site. For the cost of one night’s lodging, they bought a year membership with TrustedHousesitters. This site is one of a half-dozen international housesitting operations that allow travelers and homeowners to swap services. Homeowners get free pet-sitting and plant watering from travelers, who get free accommodations in exchange.

When SideHusl.com editors caught up with Ilagan and Cassaniti, they were housesitting in Costa Rica. Video-conferencing in front of a picture window, our editors could see monkeys swinging through the trees behind them.

“One month of my life in Chicago cost the same as traveling the world for an entire year,” says Ilagan.

International housesitting

However, there are a few things you need to know about international housesitting. First, it’s important to stress that this is not a “job.” If you want a job overseas, you generally need to get a work visa.

And getting a work visa is both time-consuming and uncertain. That’s because countries don’t want foreigners to take jobs from permanent residents.

TrustedHousesitters devotes an entire section of its website to explaining how housesitting differs from paid work. And, it even offers form letters to present to border control agents, when there’s a problem. But it’s best if you simply skirt the issue completely.

This is easiest to do when you plan ahead, booking not only your current sit but the one after that, too. Ilagan says planning months in advance also gives them the ability to book cheaper transportation.

Going through customs

Every country asks tourists to answer a few questions on arrival. One is whether you’re traveling for business or pleasure. And another is where you’re staying while in the country and for how long. Finally, customs agents want to know where you’re going when you leave.

You should be sure to say that you’re tourists. Also have the names and address of the people you’re housesitting for, and a plan for where you’ll go next, when, and how. If you have a return ticket, great. But, if you’re going on, you can also explain that you’ll be leaving the country via car, boat or train.

This should satisfy customs officials. The fact that you’re watching someone’s pets may never come up.

Housesitting full-time

While there are many housesitting sites that you can sign up for, when you want to housesit full-time, TrustedHousesitters is the best choice. There are several reasons why.

One is that the site is far larger than its nearest competitor, which means there are more houses available in more countries. In addition, where most housesitting sites simply charge a flat rate to join, Trusted offers premium plans that provide valuable services to people who travel and housesit frequently.

For instance, the site’s standard housesitter plan costs $129 annually and provides a background check and unlimited access to housesits for a year. However, for $259, the site offers a premium plan that offers airport lounge passes; online and video chats with vets; and liability insurance. This plan also includes “sit cancellation insurance” which pays you up to $1,500 if a homeowner cancel a housesit at the last minute and leaves you homeless.

Since homeowners do sometimes cancel plans at the last minute, sit cancellation coverage allows full-time housesitters the time to regroup and find a Plan B.

Side hustles

The bulk of Ilagan and Cassaniti’s remaining monthly expenses are for food and clothing. Because they have spent a good portion of their time traveling in inexpensive locations, such as Thailand and South America, they can eat and dress well on a relative pittance — about $500 a month.

But, they still need to make some money. So they looked for side hustles that they could do from anywhere at anytime of the day or night.

The couple engages in several side hustles, including selling photos and videos. Selling photos seemed like a natural fit, considering that they’re traveling and snapping pictures all the time.

Sites like Alamy, Adobe Stock, and Getty Images invite freelance photographers and videographers to upload images for stock photo buyers. When an image sells, the photographer earns a royalty. Similarly, print-on-demand sites such as FineArtAmerica and Society6 can use photographs to decorate products ranging from iPhone cases to prints. They, too, pay royalties to the photographer for each sale.

The couple also launched a website called MapTheUnknown, which they hope to monetize with advertisements, affiliate marketing arrangements and by using it to sell their life coaching services.

Other nomadic hustles

However, there are dozens of side hustles that are ideal for people who want to quit work and travel. These include writing and editing; tutoring; transcription; website testing; consulting; and translation.

All of these jobs allow you to set your own schedule and conduct your work from anywhere that you have an internet connection and a laptop.

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