How Jessica and Her Boyfriend Worked Their Way Around the World

Updated: 12/05/19 | December 5th, 2019

One of the things that keeps people from traveling is money. They either don’t have enough, don’t think they can save enough, or fret about coming home with not enough. It’s easy to think “I can’t travel, I don’t have money,” but there are a lot of ways to travel without leaving with a small fortune.

I taught English while living in Bangkok to fund my travels and keep myself on the road. Last month, we met Arielle who worked on yachts to travel the world; this month we meet Jessica and her boyfriend Brent (no relation to the Jessica in this post) and learn about how they work odd jobs overseas to pay for their travels.

Nomadic Matt: Tell everyone about yourself!
Jessica: I’ve been traveling through Europe and Asia with my boyfriend Brent since September 2011. Our original plan was to spend 15 months on the road and then move back to Canada.

Within the first few months, however, it became clear to both of us that this trip wasn’t going to be a one-off experience with a set end date. Traveling changed our goals, values, and expectations in ways that we never anticipated.

Now, we travel slowly, finding volunteer and work opportunities as we go, and spend several months in each country we visit.

What inspired you two to take your trip?
We had graduated university, started our first “real” jobs, and basically settled into lives as responsible adults. But we realized that we were at a point where we could suddenly lose 10 years in this routine: coasting along, working the same jobs every day, and drinking at the same bars every weekend.

Or, we could jump off the traditional track toward promotions, babies, and a mortgage, and instead live our lives the way we had always wanted to.

We chose the latter.

How did you go about planning your trip? Was your original intention to work and volunteer overseas? If so, how did you go about finding opportunities to do so?
We heard about WWOOFing through a friend of Brent’s, and this helped us to discover other work exchange programs, like Workaway, Helpx, and Worldpackers.

We ended up preferring these exchanges over WWOOFing because they offered a more diverse range of places to volunteer, including B&Bs, hostels, and homestays. We contacted dozens of hosts and tried to arrange longer-term stays of a month or more. We reasoned that the less often we moved from host to host, the lower our overall costs would be.

So volunteering was always part of our plan, but the countries we visited arose spontaneously. We emailed hosts in countries that interested us and then went wherever we found families that were open to having us live and work with them.

Where did you go on your trip?
So far we’ve been to France, Spain, England, Ireland, Italy, Germany, the air Netherlands, Southeast Asia, Indonesia, the Philippines, and Japan.

Next, who knows? I’d really like to branch out to South America or even Australia.

How did you save for your trip?
We spent five months saving for our trip and ended up with around $6,000 between the two of us. Through our Workaway and Helpx arrangements, we knew our host families would be providing us with three meals a day and a place to sleep. This strategy significantly reduced how much we needed to save before leaving.

During the months we spent saving in Canada, we were able to move and sublet a smaller apartment, which allowed us to save a few hundred dollars in rent each month. I started taking on extra projects through websites like Upwork to supplement the income from my full-time job.

Through Upwork, I was hired on for a one-year contract editing documents for an osteopathic training school. This job helped with our pre-trip savings, and I was able to carry on with the project when we started traveling.

This wasn’t part of the plan initially, but it ended up providing a small income for the first six months of our trip. Just before leaving, we also sold all of our furniture on Craigslist because it wasn’t practical to store it for an indefinite period of time anyway

Did you find it hard to scrimp and save?
It was surprisingly easy. It didn’t feel like we were scrimping and saving because most of the changes we made were quite small. Again, we had set a much lower financial target than I think most long-term travelers do, because we always planned to volunteer and work throughout our trip to help manage our costs.

How long did your savings last? Was the what sort of forced you to look for higher-paying work?
Our savings lasted for a little under a year in Europe, and then we were left with a choice: go home or find jobs.

Working overseas also appealed to us, because it was an opportunity to continue traveling slowly. I feel like a week or two isn’t enough time to fully experience a country. It’s awesome to have a temporary home base from which you can spend months really diving into a country’s food, culture, and language.

What did you do for work?
We taught English in Thailand and now we teach in Japan.

How did you find that job?
A few of my friends had taught in South Korea, and they recommended searching for jobs on Dave’s ESL Cafe. We found dozens of teaching jobs all over the world posted on these job boards every day.

Not every job was a gem, of course — we had a few interviews with shifty recruiting agencies and unsettlingly desperate schools. But within a few months, we were both hired to teach 3- to 12-year-olds in Thailand.

Teaching was kind of a shock at first since neither of us had even taken a TEFL (Teaching English as a Foreign Language) course, but overall it was a fun experience. We used the same job board to find our current jobs teaching children and adults in Japan.

In both cases, our employers helped us acquire work visas and housing, so the whole process was relatively easy once we found companies that we felt good about working for.

How did you manage to stay on budget while traveling?
We try to live like locals when we’re traveling because anything geared toward tourists is almost always going to be overpriced. That means figuring out how locals get around, whether it’s by public bus, scooter, or jeepney, as well as skipping restaurants with air-conditioning and English menus, and going for street food instead.

The same goes for accommodation: sometimes we stay in hostels, but more often we stay with locals we meet through Couchsurfing or Airbnb.

Even still, budget travel feels like a constant work in progress for me. I’m always looking for ways to do it even more effectively and save even more.

What’s it like traveling as a couple? How do you avoid not killing each other?
There’s no question that it was challenging at first. A lot of people will tell you that traveling together makes or breaks your relationship, and it’s true.

It’s hard to prepare for the experience of eating, sleeping, working, and doing everything else together all the time. Plans rarely unfold perfectly when you’re on the road, so our ability to work through challenges together is constantly being tested.

We try to forgive each other quickly and not hold on to grudges after an argument. We’ve had to learn to be comfortable saying absolutely anything to each other and how to ask for space when we need it.

What advice would you have for people trying to do what you did?
If traveling is something you want to do, then there are a million different ways to make it happen. For me, initially, the biggest barrier was money. I think this is the case for a lot of other people too.

But once I started researching, I realized that there are limitless ways to travel without spending a lot of money, and even ways to make money while traveling: teaching English, house-sitting, au pair work, Couchsurfing, work exchanges, and working holiday visas are just a few ideas.

Find which approach works best for you, and then there’s literally nothing to hold you back.

Like Arielle and countless other people, Jess and Brent learned that there are a lot of ways to travel overseas when you don’t have any money. Instead of letting their lack of money get them down, they found ways to make up for it by reducing their costs and finding work abroad.

It may always appear that we need to save a lot before we travel, but if we are flexible, creative, and willing to work or volunteer for room and board, we can make up our monetary deficit and extend our time on the road.

As they say, where there’s a will, there’s a way.

Become the Next Success Story

One of my favorite parts about this job is hearing people’s travel stories. They inspire me, but more importantly, they also inspire you. I travel a certain way, but there are many ways to fund your trips and travel the world. I hope these stories show you that there is more than one way to travel and that it is within your grasp to reach your travel goals. Here are more examples of people who found work overseas to fund their trips:

• How Oneika Found Teaching Jobs abroad
• How Arielle Got a Job on Yacht
• How Emily Taught English to Fund Her RTW Adventure
• How Michael Saved $14k in 6 Months Making $9 Per Hour

We all come from different places, but we all have one thing in common: we all want to travel more.

Make today the day you take one step closer to traveling — whether it is buying a guidebook, booking a hostel, creating an itinerary, or going all the way and buying a plane ticket.

Remember, tomorrow may never come so don’t wait.