Interview with Teacher Diane-former student, soccer phenom and world traveler

hiking in ecuador

Diane hiking in Ecuador

Another former student of mine has embraced the world of travel, location independence and global citizenship. In her youth,  she was my 11th grade student, a soccer phenom and president of SADD while I was the advisor. As the president of SADD, we spent many hours after school organizing activities and volunteering with heaps of other students, adults and organizations. As many who graduate high school and enter university and then the workforce, Diane took opportunities afforded to her to see the world at an early age. Finding just as much joy in the world outside of the town in which she grew up as she did when she resided there, she took off to see cultures far from her own and live outside her comfort zone. Recently, thanks to social media, we reconnected, and discovered a shared love of travel! Here she shares her story of what she believes to be the gifts of travel.

1.When did you get started traveling? My first time traveling abroad was the summer of my sophomore year in college, when I studied in London. Before that, I had only traveled around the United States.

2.What made you decide make the jump to a location independent/travel-based existence? I spent a year volunteering at a physical therapy clinic where I spent a lot of time working with geriatric patients. In that year, I learned a lot about physical therapy, but what struck a chord with me were the stories that the patients shared with me about their lives, their dreams and their regrets. “You’re so young,” they would say to me. “I wish I were your age. I would travel more…” This statement really resonated with me. I wanted to find a way to travel while I was still young, but I wasn’t ready to spend all of my money. I searched online for the best ways to travel for free, and learned about teaching English abroad. Less than a month later, I received my online TEFL certification, and was on a plane headed towards a small town in Brazil. This experience not only taught me that it was possible to save money and travel at the same time, but, it also taught me about a passion I never knew I had: teaching. I spent six months teaching English in Brazil, and then another two years teaching English in Chicago. Working with students from all over the world only added to my desire to travel and experience first-hand all the things I was hearing about from others. I realized that I would never be able to truly experience all I wanted to experience with the traditional 9-5 job, and two weeks vacation per year. With the encouragement of my family, boyfriend, friends and former students, I decided to quit my job and start my own business, teaching English online. I had always thought that teaching in person was much more beneficial than teaching over the Internet, but once I learned about all the resources available to me online, I realized I could be location independent and continue to do what I love.

3.What benefits do you feel you get from this lifestyle? How do you handle the nay-sayers in your life? The benefits that I get from this lifestyle are endless. There’s the freedom to live wherever I want and work without a boss, the flexibility of making my own schedule, the constant challenge of adjusting to new surroundings, the ability to see the world from different perspectives and learn about others as well as myself. There will always be people who question when you choose to live a non-traditional lifestyle, and I’ve learned to accept that. I often encounter people who feel as if I am judging them for not living their lives in the same way. But, I’m not! I know that the way I choose to live my life isn’t the best for everyone. There are some comforts that I am willing to give up in order to live my life the way that I choose, and I understand why others aren’t willing to do the same.

4.How did you save money to be able to afford living ‘on the road’/traveling often? How long did it take you to make the jump to a location independent/travel-based life? I have always been a saver, and I love looking for news ways to travel cheaply. When I first started traveling, I used websites like and, which offer free accommodation in other people’s homes, in exchange for offering your home in the same way. These websites not only provide me with a free place to stay, but are also a great way to be quickly exposed to the culture and way of life of each place I travel. However, these websites can only be used for short trips. So, when my boyfriend and I decided to live abroad full-time, we couldn’t rely on them. Rather than spending years saving up enough money to travel, my boyfriend and I decided to start by living in cheap destinations. We browsed the Internet for lists of the best retirement destinations, and decided to start there. In Cuenca, Ecuador, we lived for six months in a beautiful apartment in the center of the city for $350 a month. In Chiang Mai, Thailand, we did the same. For shorter trips, we find accommodation using AirBnB. Best of all, because I use the apartment as my home office, I can write off part of my rent as a business expense! We know that in some places, rents that low are impossible to find. So, this year my boyfriend and I are trying housesitting for the first time. We’re currently in an apartment in Istanbul, where we’re staying for free for a month in exchange for looking after cats. Next month, we’re headed to Belgium to do the same. There are a lot of ways to travel frugally-you just have to make the effort to find them.

dan and i (thailand)

Dan and Diane in Thailand

5.How do you choose your destinations and for how long you’ll stay? What type of accommodations do you typically choose? Are there any specific resources you recommend? Because both my boyfriend and I work online, one of the most important factors in choosing a place to go is the quality of Internet. Of course, we also consider the weather, public transportation systems, safety and affordability. My students and fellow travelers we meet often recommend places to visit. We stay until there’s somewhere else we’d rather be, or until our visa expires. We tend to stay places 3-6 months at a time to get a real feel for life where we are.

6.How much money do you traditionally need annually to support this lifestyle? Over the past two years, my boyfriend and I have spent about $1000 a month (each), on average.

7.How do you make money on the road and save for retirement? In January of 2013, I launched my own business,, with the almost idealistic dream of being able to travel the world and teach English on Skype.  I am fortunate to say that over the last two years, I have made enough money to not only fund my travels, but also to save for the future. I currently have three English teachers working for me, whom I met in my travels, and together we have taught students from over 30 different countries.

8.How do you handle visas, vaccinations, legal documents/passports, taxes and healthcare while living without a home base or an ever-changing one? As a US citizen, getting tourist visas are quite easy. Additionally, having supportive parents helps a lot. My parents allow me to use their home address as my own while I travel, and they email me any documents I need that arrive in the mail.

9.If you decide to settle somewhere – where and when do you think it will be? Unfortunately, along with all the benefits of travel comes “the traveler’s curse.” This is the idea that the more places you see, the more things that appeal to you, and the more you realize that no one place has them all. This quest to find the place that is perfect for me has gotten increasingly harder as I travel more. Another part of the traveler’s curse is the inability to cultivate long-term relationships as you’re constantly on the go. Because of this, I have accepted that I won’t be able to live like this forever. I know that eventually I want to start a family and settle down in a city (or on the outskirts of a city) close to my family and friends. My boyfriend and I are currently thinking about settling in Boston in the future, and only traveling for a short time each year.

10.What advice do you have for others trying to make the jump to a location independent/travel-heavy lifestyle? I have been lucky to have very supportive friends and family who made the transition fairly simple for me. My advice would be to save up enough money that you feel comfortable living on for about a year. Design a business plan, test it out, and then just go for it! If you wait until the moment that you feel 100% ready, that moment might never come.

11.In your experience, what have been the two most significant gifts of travel? Travel has given me the opportunity to see the world from other perspectives. It has exposed me to many new ways of life, and made me more open-minded, tolerant, and self-confident.

bike trip

Life on the road

I have been lucky to connect with many students over my teaching career. Watching them continue to find their way and fly is a true pleasure and reconnecting later in life continues to be a gift. If you’re interested in learning more about Diane, check out her website.

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