How I Paid for 20 Years of Continuous Travel

This year marks 20 years since I first left the US for Japan in 1999 to live abroad and travel the world. Ten years ago people where wondering how I could travel so long. After another 10 years most people in my life see my lifestyle as normal, while others I meet assume you have to be successful first to achieve it. Nothing could be further from the truth.

Recently a number of people couldn’t get over how cool my life seemed and asked EXACTLY how I managed to piece this international lifestyle together. Because flattery works every time on me, I decided to update my original post from 10 years ago. Here is the road map for how I managed to travel the world, do what I love, fall in love, have a family and get paid for it for 20 years. 

For those of you who don’t know my background, I left the US in 1998 to visit Japan on a study abroad program in Osaka. Coming from a middle class family, it was my first time on an airplane and I was 21 years old! Over 50 countries (I’m sure I’ll forget to mention a few below) and countless jobs later I’m still on the road, now with my wife and two children (6 and 8 as of 2019).

WARNING: This is a long post.  For word nerds, it is exactly 3,119 words long. For time nerds, it will take the average reader 15 minutes to read and 10 more seconds to understand. Proceed carefully. It might cause you to change your life.

We Want the Dirty Details including Money, Money, Money…Money!

I know that it can be difficult to relate to such a life sitting behind a pile of bills, late payments, and screaming kids demanding your attention. I was sitting in my hometown bar a few years ago reminiscing with a buddy about the countries he visited me in. A hard drinking, hard working local took exception:

“Who the fuck do you think you are? Stop lying, no one could have been to so many places.

What are you 30 years old? [I was 28] Get the fuck outta hea (that’s New Englander for “here”)”

My sister was bar tending that night and told him to quite down. Drunk Dave turned quiet, grabbed his beer tighter and just repeated softly “it’s just not possible”.

Well it is possible, but I’ll be honest, it does require a number of sacrifices, leaps of faith, and the ability to go against the collective wisdom of just about everyone you know and love.

I try not to speak too much about money here, since I do like to maintain some privacy given how much I put myself and my family out there. But it is important for this post to be useful, and it can only be useful if it is honest. I’ll show you just how little you really need to travel the world, and that you don’t need to sacrifice your future for your dreams. As you will see, you can do it while heavily in debt, you don’t need nearly as much as you think, and long-term travel doesn’t have to equal abject poverty. In fact, due to lower costs of living, beneficial tax breaks, and a personal desire for simplicity and lack of acquiring “things” I think I have led a higher quality of life outside of the US than I could have if I stayed (wars and bombing raids included).

1998- Study Abroad in Osaka, Japan

In 1998 I was all set to go on my university’s study abroad program in Japan. At the last minute it was canceled as there were only two people signed up. Undeterred, the two of us created our own program, found a school to enter and arranged everything ourselves. I was a poor collage student, paying for my school all on my own through student loans and scholarships. I saved roughly $1,000 for extra expenses through my part-time job. Somehow, I thought that would be enough for 4 months of living expenses in Japan.

Luckily, as we organized the whole trip ourselves I had to pay the tuition upon arrival. Japan is a cash society so I carried $12,000 in traveler checks (yeah that is a lot of $100 checks!) with me on the plane. As I flew over the Pacific Ocean for the first time the exchange rates went crazy and when I landed I didn’t need all $12,000 to pay for school and was able to use the savings to live and travel.

I also cashed in a $1,000 in inheritance to pay for the 900 mile, 88 temple walking pilgrimage I went on after school ended. Yes, the same one I’m now publishing a book about. Life has never been the same since.

Counties Visited: Japan and Jamaica (yes, spring break called)

Money Saved: Nope. Maybe your expectations are too high for me.

Balance Sheet: Sinking further and further into student loan debt.

1999-2001 Shiga, Japan- JET Program

I was lucky and graduated university with only $30,000 in debt. Yes, Gen Z and Millennials, we also had student loan debt way back when!

After graduation I got a job as an assistant language teacher with the JET Program in Japan. This was a fantastic first job and I earned roughly $36,000 per year. I got 20 days of paid vacation, left work at 4 p.m. everyday, and didn’t have to work over the summer. I spent all of my money traveling around South East Asia, and exploring Japan. Since I lived in a village of  only 8,000 people my Japanese got way better than my expensive university ever managed to help me with.

Counties Visited: Japan, Spain, Vietnam, Thailand, South Korea

Money Saved: $0

Balance Sheet: -$30,000 ++ in student loan debt (interest is a tough master)

2001 Peru, Parent’s Attic, Chiba-Japan- Private English School

After two years in Japan I was looking for a change and returned to the US. I didn’t have a job so I moved back in with my parents and lived in my old room. Despite not have much money in savings I headed down to Peru for a few weeks to hike the Inca trail and explore the Andes Mountains.

I decided it was better to be work abroad than be unemployed in the US and found another job teaching in Japan again. This time it was for a private English school that paid me even less money, $30,000 a year, to live in Chiba (near Tokyo).  The Tokyo area is as expensive as you can imagine, but I stilled traveled and managed not to save any money. I kept paying the minimum on my student loans and saving money for travel.

Countries Visited: USA, Peru, Cambodia, Laos, Singapore and Thailand

Money Saved: $0

Balance Sheet: -$30,000, getting a bit tired of treading water!

2002-2004 Shiga, Japan- Elementary School English Teacher

Living near Tokyo just wasn’t for me, nor was being broke and stressing about bills. So, I called in some contacts and found a new job back in my old area of Shiga Prefecture, Japan. Getting back to the Japanese countryside was great as was the return to my JET salary of $36,000 a year. Money and free time went to paying for jaunts to South East Asia as well as slow travel around Japan.

Countries Visited: Japan, Thailand, Myanmar

Money Saved: $9,000

Balance Sheet: Getting smaller. -$20,000 still in the hole.

2004-2006 Graduate School in Boston, Thailand and Japan (yes again)

Five years after graduating I was out in the world but making the same amount of money as when I started. I was also chained to a job and was only able to travel during vacations (of course living in Japan was nice). I was growing restless and it was clear that teaching English was never going to fulfill me. It was time to make a change. I got into graduate school for International Relations and moved to Boston (yes, that is a longer story for another time).

I visited Japan (yes, an ex-girlfriend) over winter vacation, broke up and then for the summer between year one and two I took an internship in Thailand. I lived in Bangkok for 2 months, toured the country, visited Cambodia again, and then headed back to Japan for 1 month to walk the Shikoku Pilgrimage, again. I paid for it with a $2,000 grant and a work for shelter agreement with the NGO where I volunteered.

I paid for two years of graduate school the only way I could, I took out massive amounts of loans (private and government subsidized), blew through the $9,000 I had saved, worked part-time, and maxed out credit cards, and then maxed out some more.

This was a huge gamble. I took out over $100,000 to go into non-profit work! In the end I decided I would rather live the life I wanted and owe money than be miserable with a mortgage Looking back with a bit of insight in life, these probably weren’t my only choices!

Countries Visited: USA, Thailand, Cambodia, Japan, Canada, Las Vegas (trust me it’s like another country)

Money Saved: Ha!

Balance Sheet: Took a beating, -$120,000 in debt (Credit Cards and Student Loans)

2006 San Francisco, Timor-Leste (East Timor)- Intern, Governance and Conflict Consultant

When you are $120,000 in debt, what is the smart thing to do? I clearly didn’t know. Whatever it was, I did the opposite and took another internship, this time in the expensive city of San Francisco for three months. I was paid exactly $3,000 to keep me alive and barely breathing. I cobbled together a string of couch surfing and sublet agreements and slept in five different houses over the three months. I managed to drive the length of route 1, party in La Jolla for the 4^th of July, and enjoy Big Sur on the way back.

The phone rang one day, one week before my contract was up, and I was offered a one month assignment in Timor-Leste (yes, the number “one” seems to be important here). I said yes without the .slightest hesitation, dropped a bag and flew out a few days later with no intention of returning to the US. I lived in Timor for 6 months, traveled the country, and explored Bali and the rest of Indonesia.

Oh, by the way, Timor-Leste is where I met my now wife!

Countries Visited: Timor-Leste, Indonesia, Sri Lanka, Singapore

Money Saved: Just glad I was able to start eating again.

Balance Sheet: Still -$120,000 over my head.

2007-2009 Sri Lanka (the civil war years)- Human Rights Advocate

With a few months of experience under my belt in my new profession I followed a girl (now my wife) to Sri Lanka right when the civil war was starting back up. It took me about three months to find a job, after being broke and down to my last dime. But I found one, threw myself into work as a human rights advocate, and eventually turned it into a Country Director position. The NGO had no idea that I was going to do that, but it just shows what you can accomplish if you try something new.

During this time we enjoyed the hell out of Sri Lanka and I got to start traveling for work and adding fun to the end of each trip. It is an amazing thing to get paid to travel! But I knew I needed to get my finances in order. Unless I paid down my debt I’d never have a future. So I created a plan I cashed in a $10,000 inheritance I came into and paid off my credit cards, rolled the monthly interest savings into my student loan payments, started saving for retirement, an eventual house, travel, and food when I had a chance.

Yes, I learned to budget. It is probably not the secret you were hoping to hear.

I did all of this making $38,000/year and and finished out my time there making $47,000 a year. But with no taxes and low cost of living, life was good.

Countries visited: Sri Lanka, Maldives, India, Thailand, Cambodia, Malaysia, Switzerland, England, Japan, Dubai, USA

Money Saved: Probably about $15,000 over three years.

Balance Sheet:I still owed about -$89,000. But I was beginning to learn to how to swim.

2009-2011 Kosovo- Consultant, Peacebuilding, Rural Tourism

The war finally ended and it was time to move on. We did the only sensible thing and my wife and I packed up and moved the Balkans. She took a job with the United Nations and I followed her and started consulting. When consulting work dried up I landed a job also working for the United Nations in the divided town of Mitrovica in Norther Kosovo. I moonlighted pro bono writing a hiking guide to southern Kosovo and writing more travel articles. Yes, this was the beginning of combining my travel writing with development work.

Let’s just say working for the UN in a non-family duty station (yes, I had my family with me) is very good for the bank account. From here on out my career takes off a bit, and numbers are too fresh for me to be specific. But working for the UN I was making over 100k a year.

Between the UN, consulting, and having a baby boy in Japan I did quite a bit of traveling these three years. Despite my income increasing, I always assumed I’d go back to a lower NGO salary. So I kept my “normal lifestyle” and used the extra money to aggressively pay off my student loans, save for a house and…you guessed it… travel.

Countries visited: Singapore, Timor-Leste, Sri Lanka, Austria, Kosovo, Turkey, Macedonia, Montenegro, Albania, Croatia, Slovenia, England, Netherlands, Jordan, USA, Japan, Maldives, Bosnia and Herzegovina, Bulgaria, and Italy

Money Saved: $50,000

Balance Sheet: I owed about $36,000 in student loans. I paid off all private loans with high interest rates and continued the practice of never carry credit card debt into the next month (ie never going back into debt), and the rest of the loans were at a low 3.25% interest rate. My plan was to pay the minimum payment for the rest of my life and put the rest of my savings into investments. Every time I make a plan, something else happens…

2012-2018 Timor-Leste (yes again)- Community Policing, Land, Management

With the birth of my first son it became clear that the pollution in Pristine was not good for his little lungs. Despite having work offers in Kosovo, we decided to move back to Timor-Leste. This time my wife followed me as I took up a job with an NGO managing a community conflict prevention program focused on community policing. I took a pay cut down to $70,000/year compared to the UN, but you can’t put a price on doing what you love, in an organization that you love. Plus it was more than enough for us.

One year into life in Timor-Leste the student loan companies had pissed me off one too many times with their fees, and making it difficult to actually pay. So I took my house savings and paid off the full balance. We were debt free, and I felt more free than ever. I’m not sure that I ever really believed that day would come. But I will remember the feeling of sending in my last payment and feeling like I was finally sticking it to them. I was able to really decide what I wanted to do in life, and change when I wanted.

Twice we decided it was time to leave Timor-Leste, and twice I was promoted and we stayed. If I had only been worried about money I probably wouldn’t have been in a position to ask for what I wanted, directly and without emotion. I was able to ask for more because I felt secure in knowing what I wanted and that I had the means to support my family. This was a great seven years for our family and we added a daughter to mix. But, we knew when it was finally time to leave so we set about making it happen. It took year of planning and 10 months living a part but we did it. Next stop….

Countries visited: Singapore, Timor-Leste, Thailand, Sri Lanka, Maldives, Indonesia, New Zealand, Australia, Japan, USA, Austria, Germany, Philippines, Holland

Money Saved: We are getting too personal here. Let’s just say I no longer need to keep track of this part of my life any more.

Balance Sheet: Positive 🙂

2019-Present Lao PDR- Country Office Management, Dream Job

We are now living in Laos and I’m managing the country office of an international non-profit. There is not much to say other than we love it. The kids are in international school, the work is interesting, the staff are amazing, and the last thing on my mind is money. We are enjoying being where we are, doing good in the world, and making the workplace the type of place we want to be. We never make plans, but mentally we will be here for 5 years or so.

Countries visited: Laos, Indonesia, Singapore, Japan, USA, Thailand, Vietnam, South Africa (so far but it has only been 7 months!)

Money Saved: Way too fresh to share. But my same basic plan I made back in Sri Lanka is still working for me.

Balance Sheet: Still positive 🙂

You don’t have to be Rich, or Poor, to Travel the World

I don’t expect you to run out and follow my life step-by-step. But I hope that you realize that traveling the world, or doing anything that you love consistently, is a decision that you have to continually make. Sometimes you will have money, other times you won’t. That is the nature of having a free life, but even freedom requires choices and planning. But it can be done. I’m still doing it, my wife is doing it with me, and now our son and daughter are 7 years into our party. Besides the travel aspect we are doing the type of work we love, making a difference in the world, and getting paid for it.

Looking back now after 20 years I can see that the bumps in the road, the set backs, and the many times I was scared shitless as I went against the grain where not that dramatic after all. With a solid plan financially, a focus on working hard at the things we love, and remembering to enjoy where we are, we were able to make steady progress toward not just mental freedom but also financial.

Never underestimate the value of living in a cheap country, spending less than you make, and following your dreams!

What are your secrets for traveling the world?