How 2 People Traveled for a Year on $20,000

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At first glance Evo Terra and Sheila Dee’s story might seem a lot like many other empty nesters who sold everything to travel around the world. But most weren’t kicked out of their home state by a doctor—and most eventually return. These two are still going!

Here’s their story:

We’re Evo & Sheila, now collectively known as ShEvo or The Opportunistic Travelers.

After 17 years of living in Arizona, Sheila’s doctor told us to leave—the quicker, the better. The dry, dusty atmosphere was quite literally killing her. So two months later, we found ourselves on a plane bound for Europe, chasing high-humidity environments and seeing what living as travelers and expats is like around the world.

Prior to this trip, we hadn’t done all that much traveling, except for the standard up-to-Canada and down-to-Mexico trips most people from the U.S. make every year or so. Because there’s something extra motivating when a doctor orders you to get out, we decided to really go for it and try out a few other continents!

Costa Brava, Spain

Getting practical: how we finance this lifestyle.

Last year’s travel was almost 100% financed by the sale of a car. I did a small amount of consulting work on the road and picked up a paid speaking gig or two, adding a few more bucks to the kitty for a total of about $20,000 USD. That’s not a huge annual travel budget for two people who aren’t backpackers and like eating things other than instant noodles.

So last year we let housesitting assignments determine most of our itinerary. After 12 months, 13 countries, and 3 continents we spent less than 30 days in paid lodging. Plus, we got to see some areas of the world where not all that many people have traveled.

Phuket, Thailand

How did we pull that off? Here’s our step-by-step process (that we actually followed) for becoming successful house sitters.

Step 1: Fish Where The Fish Are

House sitting assignments just don’t fall out of the sky. You have to be in the marketplaces where homeowners are looking for sitters. Luckily, almost all of this happens online these days. Your first step is making a profile on various housesitting services. We strongly recommend creating profiles on many of them. Don’t put all of your eggs in one basket, as different sites attract a different sort of clientele.

Step 2: Make Yourself Look Good

By “yourself” I mean your profile. Fill it out completely. More is better. Even if you (like us until recently) have never done this before, state your current experience. Have you owned homes before? Say that! Are you a handy person? Volunteered at your local animal shelter? Look for the things that set you apart and make you an invaluable person to the homeowners.

While we’re on the topic of looking good: use a video! All of the sites will let you upload a video. Figure out what you want to say and do it. If you have pets you can include in the video—all the better! Be authentic. Be friendly. Look like the people who you’d want staying in your house while you were away.

Step 3: Be Flexible

Not everyone travels as open-ended as we did. But even if you have a set, two-week vacation that you can’t deviate from, you might still find success landing a housesitting assignment. Start by planning far in advance. Six months isn’t too far to look. And be open to different places than the standard “vacation” spots. We would have never thought about spending three weeks at the start of winter in France, but it turned out to be an amazing experience!

Step 4: Check Listings Every Day!

Many homeowners will wait until less than a month for assignments. Others list the same needs year after year. Regardless, it’s a race against the clock once it’s posted. Without a doubt, we had the best luck getting on a homeowner’s short-list of candidates when we were one of the first applications. Look, it’s you and a bunch of other qualified people on these services. Assume the homeowner will have lots of options. It’s not enough to just be one of them. You want to be one of the first!

Step 5: Be Proactive

As soon as you get a bite—a homeowner saying they’ve looked at your profile or is keeping you in mind—try to get a call or Skype session scheduled. It gives you a chance to make a strong first impression… before anyone else! Of the times we could get a homeowner on Skype, we always got the assignment. Always. It’s truly the secret sauce.

Step 6: Don’t Give Up!

I’ll be honest: the first few weeks were pretty rotten. We had already sold all of our stuff, but no one was picking us. Then an assignment with some livestock came up. I grew up on a farm, so looking after some chickens wasn’t a big deal. And they picked us! Not long after that, our second assignment came. Then our third. Our fourth… and suddenly we found ourselves with more flexibility to choose where and when we wanted to go.

Sheffield, England

Beyond house sitting.

We were both passionate storytellers even before we started traveling. So documenting our journey sharing our life on the road was natural for us. About six months in, we started working with a couple travel brands, producing articles for them on a for-hire basis. One has since become a major sponsor of our podcast, which is currently in its third season. I occasionally write for a handful of other paying publications on an ad hoc basis.

Our most unusual revenue stream comes from postcards, oddly enough. Every month, we send out hand-written postcards to a variety of people from around the world who support us with small contributions. There’s a decent margin in Thailand, where the cost of the card + stamp combo is around $1 USD each. It’s not so great for places like Australia or China, where the cost is closer to $5 per unit. But it’s a great way to meet people as we sit around a table in a cafe or bar with a pile of postcards spread out.

We have loads of diversity built into our revenue stream. Neither of us are keen on blogging long enough to make selling ads or affiliate marketing a reality. Nor are we interested in running a fulfillment by Amazon business. So we both take on consulting projects (narration and digital strategy for me, curriculum development for Sheila), and Sheila’s putting her Master’s of Education degree to good use at an international school.

Mallorca, Spain

Do we miss life back in the States?

With very few, minor exceptions, life isn’t that much different on the road. Neither of us speak any other language than English. Yet we stick to local transportation methods. We dine in local restaurants. We shop in street markets and local grocery stores.

We both thought the world would be a lot more “foreign” than it turned out to be.

Learn more about Evo and Sheila on their website, and watch their antics on Snapchat.


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