How Travel Taught Me That Anything is Possible

By Jessie Festa

When I got to college, I wasn’t sure what I wanted to major in, so I chose Communications, because I really enjoyed writing. I thought that I could maybe do marketing, public relations, script writing, or even acting.

But even though I didn’t know exactly what I wanted to do professionally, I did know one thing for sure: I loved travel. I grew up traveling with my family, taking road trips to amusement parks in North America and cruises to the Caribbean.


Cartwheeling through life in the Exumas, Bahamas. (Photo: Jessie Festa)

And it even though I didn’t know it at the time, those trips were paving the way for a lifetime — and a career — filled with travel. But although I am a successful travel writer now, this was not always the case. Here’s how I got here — and how travel taught me the most important life lesson in the world.

Starting out Down Under

When I was a junior in college, I got the chance to study abroad in Sydney, Australia, where I got to have so many different experiences. Not only did I live, work, and go to school in a foreign place, I also explored a new country in depth and got to know its unique culture. Studying abroad is what really sparked my travel bug. I felt like my curiosity about the world was ignited.

I’d done so much in seven months, but there was still much more to do and see. Before I even returned home from the semester, I was already planning my next trip.

Doing Europe solo

The following semester, I convinced a group of my girlfriends to plan a backpacking trip through Europe for the summer. I spent hours upon hours researching where I wanted to go, what I wanted to do, and how I could spend an entire summer in Europe on a college waitress’ salary. Everyone seemed really into it. However, as summer approached, the group began dwindling. What started as five girls quickly went down to four, then three, then two — and then only me. It was then that I had a decision to make: I could either give up this amazing trip that I had spent the entire semester planning, or I could go by myself and have an adventure. In the end, I decided to go on my own, figuring that if I really hated it, I could always change my flight to come home early.

Related: Tips For Finding The Perfect Travel Souvenir

Hooked on travel

My European solo adventure ended up being one of the best experiences of my life. I fell in love in Amsterdam, learned flamenco in Spain, went wine tasting in Italy, took the ferry over to Morocco, explored castles in Portugal, island hopped in Greece, and hiked the hillside in Scotland. Everything was an eye-opening adventure, from bungee jumping in Switzerland to buying a pastry at the local bakery. I also made friends that I still talk to and see to this day, six years later.These were the types of experiences that made me feel like I was truly living.

Unfortunately, college was about to end, and I realized I would no longer be able to keep worried family and friends at bay by telling them that my wanderlust was “just a phase.” So I made a promise: As soon as I graduated, I would settle down. In my mind, then, time started to run out, because I knew that when I got a 9-to-5 job, I would no longer be able to explore the world in the way that I wanted — at least not without getting fired.


Making new friends in Bacharch, Germany. (Photo: Jessie Festa)

Buying time

In order to buy time, I went for my Masters’ Degree. My parents were really proud, thinking I was doing it to enable myself to get a better job. And while part of me was trying to set myself up for the future, the other part was giving myself a few more years until I had to “settle down.” Once I was in graduate school, I spent my summer and winter breaks backpacking solo through South America and Canada, traveling with friends to Mexico and the Caribbean, and road-tripping with a boyfriend through Colorado. I felt like I had to pack in as much as possible before graduation.

Related: How To Hack Your Next Trip


Exploring Jordan. (Photo: Jessie Festa)

Post-graduation pretending

Once I finally graduated, I knew I didn’t want an office job. I’d go on interviews here and there, but I was never enthusiastic — and always hoped I would blow the interview. When I finally did get a job, it didn’t last very long, as they wouldn’t let me have any time off for travel until I had been there for six months. And even when I eventually got the time off, it would be only two weeks for the whole year.

I loved slow travel, i.e. really spending time in a place to get to know it, and I knew that was just not going to be happening if I stayed behind a desk. I couldn’t stop thinking about how alive travel made me feel, and how stagnant I felt working in an office. I was on someone else’s schedule, following someone else’s rules. I wanted to live my best life, and do things my way.

Time to quit

When I quit, my family and friends did not approve, but travel was something I felt really strongly about. I decided I didn’t care what they thought. If they loved me, they would accept my choice. I didn’t want to be one of those people that did the same thing every day and lived a similar life to everyone else. It just wasn’t for me.

To make money, I waitressed, which was great because they let me take off when I wanted. I had a good system going: I’d waitress for five months, working doubles like crazy, and then I’d go away for three to four months and do it again. I probably could have done that forever, but I had to get my family and friends off my back — not to mention the fact that I knew I eventually wanted to do something a little more gratifying.

Discovering travel writing

One day, I stumbled upon a travel writing class online, and signed up. I loved writing, and I loved travel — it seemed perfect. As soon as I met the other students and alumni and started reading blogs, I realized that it was possible to combine my passions and make a living doing what I loved. Today, I travel as much as humanly possible. And even though I travel all the time — mainly on my own — I still have a bucket list and things that make me nervous. But once you take one step in the direction of your dreams, you’ll be able to take another.

Related: So You Want To Be A Travel Blogger?


Exploring California’s Coachella Valley with my boyfriend, Chris. (Photo: Jessie Festa)


So, what’s the message here? For starters, it can be scary taking a career break — or to decide to not have a traditional career at all. But you really need to remember that you only have one life — so do your best to live it how you want to. If you’re happy in a more traditional role, that’s awesome. But if you’re not, don’t pretend.

It took about three years for my family and friends to finally accept my lifestyle, and truly recognize how I didn’t “waste my degree.” While loved ones have given me great advice over the years, that is one piece I am glad I didn’t take. Nobody knows what you need more than you do. You just need to trust yourself enough to make it happen.

Watch: Yahoo Travel Panel: Travel As Reinvention

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