What We’ve Learned After Five Years of Travel

We used to be the type of people who started things with intention, people with an idea of where we wanted our paths to take us. Five years ago that all changed when we headed off on an adventure with very few intentions past seeing what there was to see on our savings before settling down to “adult life.” We had no timeline in mind, and when a family friend asked us incredulously “why?!” we wanted to travel the world we didn’t even have a solid answer. Now we find ourselves looking back in wonder at the path we ended up following.

Today, we are in Bali celebrating an anniversary. It has, amazingly, been 6 years since our first date, 5 years since we started traveling full-time, and 4 years since Tom proposed the last time we were in Bali. I never expected to still be traveling five years later and it has put me into a quite a reflective mood, thinking back to that goodbye dinner five years ago and how I would now answer that question.

Why do we travel?

We travel because we want to live a life we love. For us that means not being tied down by schedules or specific days of the week. We’re free to go where we want, when we want. We are free to spend our days working on projects we love; relaxing in a hammock, playing with some new friends, or hiking to explore ancient ruins. We are free to book flights on a whim. Heading to Greece to get my wedding dress made or to Mexico to eat as many tacos as humanly possible. We are free to spend time in a place exploring a passion; like yoga teacher training, glass blowing, kite boarding, or to spend way too much time in front of our computers for weeks to work on our business. Our schedule is dictated by what inspires us, not by specific hours of the day, days of the week or months of the year.

In short, we pick and choose when we want to work, when we want to explore and when we want to laze, answering to no one but ourselves.

We don’t spend hours stuck at work if we are feeling inspired by something else, like if it’s a beautiful sunny day with perfect waves breaking outside. We hardly remember awkward office politics, external deadlines and having to put on pants on days we don’t feel like it.

We travel with just one carry-on bag each that we can pack up quickly to head towards our next adventure. Over the last five years we have visited 28 countries; over the deserts of Vietnam and Peru, through the mountains in Ecuador, Japan and New Zealand, to cities in Malaysia and Australia and around Islands in Indonesia and the Galapagos, we’ve explored monuments in the U.S. and Italy and ancient ruins in Peru and Cambodia.

We’ve spent weeks kite-surfing off the windy coasts of Vietnam, exploring cenotes in the Yucatan peninsula, playing in the snow in Bulgaria and cheering on local soccer clubs in Austria. We have bathed ourselves in cold outdoor jungle showers in the Philippines, warm mud volcanoes in Colombia, a traditional haman in Turkey, an ancient onsen in a monastery in the mountains of Japan and luxury bubble baths in an outdoor tub in a Balinese private villa.

We have met new friends and reunited with old friends all over the globe.

We have traveled in every way imaginable, on horses through La Zona Cafetera in Colombia, a helicopter over the stunning landscapes of Kauai, the Shinkansen, or bullet train between cities in Japan, a motor boat to get to our temporary home, an off the grid house over the turquoise waters of Bocas del Toro, a tiny Cessna over the mountains of Oaxaca, Mexico, brightly painted busses in Central America, a luxury cruise from Japan to Russia to Canada and innumerable motorbike rides across all kinds of landscapes.

We’ve had magical experiences; sleeping on the beach in Colombia and the Philippines, to wake up and have our morning coffee in a hammock, and our breakfast out of a coconut, hiking through the Malaysian Highlands in search of the giant rafflesia flower, walking over the cobblestoned streets of Prague, diving an underwater art museum in the Yucatan, gasping into our regulators as we drifted by otherworldly sculptures and releasing baby turtles in Mexico.

We’ve stalked marine iguanas in the Galapagos islands, bathed and fed rescued elephants in Thailand, swam with thousands of manta rays and watched them throw themselves out of the ocean in apparent glee. We have seen the sun both rise and set spectacularly countless times and we’ve even visited Hogwarts!

What we’ve learned.

We’ve learned a lot in the last five years. We’ve learned what we like and what we don’t like. We’ve learned that location independence does not always look like a Corona commercial but sometimes it does.

We have learned to value relationships and experiences over things. We have learned to need less, to spend less and to spend mindfully. This does not mean that we deprive ourselves, and trust me, we never feel deprived. We appreciate the few things we have instead of being bogged down by our possessions. We research carefully to find the best prices on flights and other travel deals and we never get rid of something until it is completely unusable. We’ve also learned that limited space will cure any hoarder; we can’t get something new unless we are leaving something behind. We have spent the last five years collecting memories rather than objects; we won’t hesitate to treat ourselves to dinner at a Michelin star restaurant but can’t remember the last time we paid a checked bag fee or bought a souvenir.

We’ve learned to play tejo in Colombia, to make chocolate in Panama and tofu in Cambodia. We learned to cook Turkish food in Istanbul, Thai food in Chiang Mai, Vietnamese food in Hoi An, Mexican food in Oaxaca, Sourdough bread in San Francisco, Colombian food in Buga and have gotten to play with different ingredients in countless kitchens across the globe. We have learned just how good food can be.

We’ve built a business together. We didn’t start traveling with the intention of creating a location-independent business and we had no idea that is what we were doing when we first started building apps together. Somehow, we created and grew both Touch Autism, our company that creates apps for children with special needs and Till The Money Runs Out, our travel blog that inspires other people to travel, from just our imaginations and hard work. And though it has been hard work, we have loved every moment of it!

I have learned that I need to write. I started this blog to keep friends and family updated on our whereabouts and adventures since I didn’t have a Facebook or other social media account. But since then it has evolved, the blog gives me a purpose in our travels, a reason to keep seeking out new experiences when I could just let travel become commonplace. A way to experience life as we go, staying in the present by thinking about how I will write about it later. It may have started as a way to share our travels but I have learned that writing brings purpose to my day to day life, helps me reflect and mull over our experiences, helps me go enthusiastically out every day to explore.

Though we choose what hours we work it is incredible how many hours we have poured into both our app business and our travel blog. We have worked in freezing cold train stations in Bulgaria, on tropical beaches in Vietnam, on the rooftop patio of apartments we’ve rented in cities like Barcelona and basically everywhere else in between.

We’ve discovered that we like working with each other, that we like working for ourselves and that we like working from anywhere. We’ve learned that we like to travel slowly and that time is on our side.

We haven’t just spent the last five years traveling, we have spent it creating, writing, crafting, building, reading, doing yoga, cooking, exploring old passions and testing out new ones. No matter what we have been doing, we have spent nearly every day together for the last five years; sometimes working together, sometimes playing together, sometimes exploring together, sometimes just relaxing together, but always together. We’ve discovered that that works for us.

What’s Next?

If there is one thing we have learned over the past five years it is that we don’t need to have it all figured out beforehand. We just have to keep being willing to reach for any opportunity that comes our way. In the words of David Bowie, “I don’t know where I’m going from here, but I promise it won’t be boring.”

87 - Tom and Jenny in Chachapoyas Peru


I think of California as officially "home" but can usually be found a lot closer to the equatorial belt. After finishing a Masters program in 2011 I found myself trying to decide between a couple of different high-powered career options. I decided I wasn't quite ready to "grow up" and went with an entirely different plan which involved selling off everything I owned with my partner Tom and buying a one-way ticket to Colombia. Our plan was to travel "Till The Money Ran Out" and then go home to start our grown-up lives. Instead, we started our own app development company on the road and have been criss-crossing the globe, traveling, working, eating spicy food and refusing to "grow up" ever since. You can find me on Twitter, , Facebook or send me a message using our About Us page.

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17 Responses

  1. Alex Crow says:

    I’m going to bookmark this piece and show it to anyone who asks me why I want to travel – I’ve still yet to leave on my own journey, but I am already getting asked “why?”

    So thank you for sharing this, it is a life-affirming and wholly positive piece that, simply put, makes me happy. Pertinent, thoughtful words, beautifully illustrated – and a perfect sentiment.

    Thank you!

  2. solosophie says:

    It’s always interesting to read what travel has taught other people and it’s lovely that you have found what works best for you 🙂

  3. Aunt Ann says:

    What a wonderful, wonderful life you two live! ❤️❤️❤️

  4. Reese says:

    Aww love this

  5. Tyrhone says:

    Great post and an impressive 6 years of travel, great that you guys have maintained and developed the same passions over the years, but I am mostly blown away by the check-in baggage thing, that is truly impressive!

  6. Joella says:

    Ahhh I loved this round up. You’ve seen so many amazing things and had so many wonderful experiences. I love how you guys gave made it work so well with your app and your air b and b- I think having that home to go back to when you want/need is key to not getting burnt out on travel. That and the fact that- like you said- you haven’t just travelled, you’ve been doing yoga, writing, creating etc. You guys have got it all sussed out I reckon. Congrats and long may you keep on inspiring yourselves and others!

    • Jenny says:

      Thanks Joella, settling down and unpacking for a couple of months no matter where we are in the world has definitely helped us to keep going!

  7. Yok says:

    Hey! Very cool post. I love the implication that location-independent entrepreneurship is characterized by problem-solving rather than simply romanticized freedom in an exotic destinations. We trade navigating office politics for navigating linguistic barriers, so-called structure and security for dynamism and curiosity…the definitive for the often inexplicable.

    Have fun 🙂

    • Jenny says:

      Thanks Yok, it certainly has been interesting figuring out not just how to run a business, but to do while traveling full time!

  8. Julie says:

    So, so, inspiring. I feel like so far I have had bits and pieces of your lifestyle, but without committing to it whole hog. I think that while it’s worked thus far, there really is something about just following life where it takes you around the world. And learning to make chocolate, and blow glass, and climb mountains. I am more committed than ever to making it a reality for myself someday

    • Jenny says:

      Thank you so much for the kind words Julie! Tom and I always compare it to jumping off into the ‘deep end’ and splashing around for a bit before we get our feet under us and realize that the water is was really only waist deep after all!

  9. What an incredible five years! So many memories made and shared, so many new skills learned and enjoyed. It boggles my mind when I hear people talk about being bored when this world is filled with endless possibilities for fun and enrichment. Good on you for making the most of your time and for showing others how it’s done!

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