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5 of My Most Liberating Travel Moments

In Blog, Storytelling by Kay5 Comments

Once upon a time, I was on the road to becoming one of those typical life stories – the college student who goes through four years of awkward dance parties, all-nighters, and busy weeks, only to start working right after college and thus losing my chance to travel independently for, quite possibly, the rest of my life. To me, that sounds like an extremely sad situation, and one that I hope will never become the story of my own life.


Travel sets you free!

But my current state of independence and proactivity has been developed over the course of over two years of traveling on my own (dang, I’m getting old) and a plethora of experiences that, good and bad, I am proud to call mine. And although I feel like I have been traveling forever, I’m only 20 years young, and I have a life of travel ahead of me ready to take off. Thanks to the things I’ve learned from my travels, I feel more comfortable being an independent explorer, and I have learned that a lot of the most life-changing experiences also require learning on the traveler’s behalf. After thinking through many of my travels and reflecting on the many life skills and lessons I’ve learned, here are my 5 most liberating travel moments:

5. Getting pickpocketed for the first time in Paris, France…and then pickpocketing the pickpocket. I was the young and admittedly stupid age of 18 when I decided to take the EuroStar from London to France to see Paris for a day. And, as I walked past a crowd of tourists, my passport got stolen right out of my backpack. You can read the full story here, but basically I found the guy a little later, holding my passport, snatched it back in a moment of terror, and was able to leave the country, passport and American identity intact.

4. Selling my car and buying a plane ticket. To tell you the truth, my mother and I had been thinking about selling this 1999 Jetta for a while at this point, but part of me really liked the convenience of having a car, no matter how old or crappy, at home. One day, my mother called me up on the phone and, after a short sigh, said, “Kay, I sold your car.” At first, my reaction was something along the lines of “WHAT?!” but instead of this outburst, I gathered myself and asked, “so now I can go the Philippines?” And I did, I went for three months, and I had the summer of my life. No part of me was thinking, during that time, dang, I should have held on to that car. It’s worth so much more than this. In fact, even if I did say that, it would have been a complete lie, because my time in the Philippines panned out to be a lot more valuable to me than any car would be.

What?! You sold my car?!

3. My first (and strangest) encounter with CouchSurfing. On kind of a whim, last fall I decided to go to Austin, Texas with my friend Dimitri. We decided to try CouchSurfing, which surely turned out to be an interesting experience. No one really knew we were going to be CouchSurfing, but our host ended up being extremely nice (if not a little bit strange). We stayed up until 4 AM talking with him and listening to his life story, and it made me truly realize that the journey is never just about where you’re going, but often times more about the people you meet along the way.

2. Creating, editing, and submitting what would become the winning video for a contest held by Nomadic Matt. Never in my life had I won anything significant until, in a frantic, 3 AM inspired frenzy, I decided to enter Matt’s competition to win a 12-day trip to Eastern Europe. And then, a few weeks later, in another inspired frenzy, I received an email from Matt himself saying I’d won. This was the first trip I’d ever gone on where I’d worked for every single aspect of the trip, all the money I needed and the things that I’d won. It was my first fully self-executed trip, and one I’ll always be proud of.

Click to watch my winning video!

Click to watch my winning video!

1. Deciding to live in Brazil for 6 months, then actually doing it. I think I must have been crazy when I decided to go to Rio de Janeiro, Brazil for a summer and a semester study abroad program, especially with a boyfriend who’d be living 5,000 miles away from me for six months and no friends in the immediate area. When I arrived, I knew no one, and although adjusting to life and culture here in Brazil was pretty hard (read: I almost gave up many times), I finally feel at home in this cidade maravilhosa.

What was one of your most liberating travel moments? What did you learn? Share your story in the comments!


    1. Author

      Haha, I definitely agree. But hopefully there are still many badass stories to come 🙂

  1. Oh, to have had those liberating moments when I was your age, Kay. I was very nearly in danger of having that life you were talking about, but at least I’m finally getting there. Better to live the dream late than never!

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