I felt so Bilbo-esque four years ago when I said to myself, “Let’s go on an adventure.” Maybe Bilbo even felt like me, as if his life should have more meaning than it did. On paper, the age of 27 saw me with a philosophy degree, a divorce, debt, a recently deceased father, and a resume that most recently included video store clerk after being laid off from my dream job. So what was the natural thing to do? I’ll tell you what the natural thing was NOT to do. It’s not to quit the only job you have to start your own business as a freelance writer/consultant, leave all of your possessions, and then travel the world without any saved money.

But I did just those things. But while I’ve been fortunate enough to travel my entire life, I always viewed travel as an end in itself, rather than a means to an end. A trip was simply the collection of experiences between the time I stepped onto the plane (or into the car) until I stepped off. I didn’t see travel as something that affected my life beyond the actual trip itself. That all changed, however, when I bought a one-way ticket to Central America.

Costa Rica sunset

When I left to travel indefinitely four years ago, I began to see both travel and my life as something of an on-going journey or story. It had its ups and downs, trials and errors, mistakes and successes, yet it was also progressing, and each moment built on the last. For 27 years I had lived a rather safe, planned out, predictable life that minimized risks. When I began taking risks it exposed me to a life that was less safe, planned, and predictable, but did so with the potential of greater reward.

During that year of travel I learned first-hand about experiences and opportunities that I didn’t even know were a possibility. I met a LGBT couple that was traveling the world by housesitting and making money from writing. I became friends with realtors in Costa Rica who were making less money than they were in America, but in a destination they considered paradise, living beachfront in Costa Rica. In Nicaragua I met locals who were creating what looked like nothing more than large clay jugs, yet was a water-purifying system bringing clean water to people who didn’t have it. What months prior was a dead end of opportunities for me was all of a sudden a highway of possibilities.

Inspirational quote sign

But as much as I learned about the world, innovation, and the people who were making life work, I was learning about myself, how to innovate my own life, and how to make it work.

It wasn’t just blind risks I had taken by quitting my job to travel, live nomadically, and work for myself. I always had multiple streams of revenue and kept enough money in my account so that if the time came to it, I could book a flight back home. To play off the William G.T. Shedd quote, ships are safest in harbor, but that’s not what ships are made for.

I think what I loved the most about that year of travel is that no two days were the same, unlike most of my prior years of childhood, high school, college, and post-college, where by and large, there was little difference from my day-to-day life. This was part of why I had left to travel in the first place. It wasn’t enough change for me to merely undergo a divorce but keep living in the same place doing the same work. True change would require removing myself from what was normal and everyday and putting myself somewhere that wasn’t. That place was Central America. As the old school Roman Stoic philosopher Seneca put it, “Travel and change of place impart new vigor to the mind.”

Overlooking Lake Okanagan

The final thing I really learned from that trip was the most important lesson. And it was that to love, be passionate, and have success at anything else in life, you first have to know and love yourself. Prior to that trip, I didn’t really know who I was or what I wanted. That trip began to tear away the layers of who I wasn’t and show me who I really was, what I was passionate, and what I had to do to get it.

Some of this about who I was and who I wanted to be I had learned from reading (and re-reading) The Last Lecture, by Randy Pausch. There are a ton of quotable lines from the book, but the two that I most frequently quote are the following:

The brick walls are there for a reason. The brick walls are not there to keep us out. The brick walls are there to give us a chance to show how badly we want something. Because the brick walls are there to stop the people who don’t want it badly enough.

We cannot change the cards we are dealt, just how we play the hand.

As important as these were, of equal importance was not just about playing the best hand, but knowing when to hold, and when to fold. There came a time in Costa Rica when I simply felt like it was time for me to go back to the states, though it was far sooner than I had anticipated, and though I had the means to either continue living in that beach town in Costa Rica or travel around for many more months. But to have done so would’ve been a disservice to both myself and the world, as I felt like I had really accomplished something, and now I could take those things I had learned and apply it to a new life I could build. And so I left Costa Rica for a short trip to California, and haven’t left the west coast since, living nomadically and freelancing ever since.

Take calculated risks. Embrace change. And follow your passions and intuition, while knowing when it’s time to move on. Those are a few of the principles that I learned from that year of travel that have largely guided my life and career for the last three years. It took me to San Francisco for a year, where I built my writing portfolio and consulted with travel brands on social and content strategy. From there it was to Seattle, for what has been my most satisfying work to date, building the Expedia Viewfinder blog program from scratch. Pitching their Director of Public Relations (thanks to Twitter), Sarah Gavin, the day before Thanksgiving, my contract was originally just two weeks. That was nearly three years ago. I’ve been working with them (among other travel brands and publications) to build their digital footprint ever since.

San Francisco from Twin Peaks

That brings me to present-day, where I now live in Los Angeles, in West Hollywood, where I’ve continuously lived longer (14 months) than anywhere I’ve lived since I was 18. For the first time in a decade, I feel like I’m home. I’m a California resident. I’m no longer a nomad. I’m dating. I have a group of friends who we refer to each other as family. But that may all seem to fly in the face of my principles of taking calculated risks, embracing change, and following my passions.

Except it doesn’t. As of this week, on Halloween no less, I leave my post as the Editor-in-Chief of the Expedia Viewfinder blog. My eyes well up when I think about the last few years. I feel more satisfied, accomplished, and proud of my life than ever before, because of my work, but more so, because of who I’ve become. That twenty-something who threw a backpack over his shoulders four years ago to travel was a different person than who I look at in the mirror today. And I wouldn’t be who I am today without that year of travel and the last couple years of living and traveling nomadically. Simply put, this is because of timing. And because I want to continue to take those calculated risks, embrace that change, and follow my passions. I’ve still got a lot more risks to take, change to embrace, passions to pursue, and work to do. But first, I’m going to take a vacation.

I went to the woods because I wished to live deliberately, to front only the essential facts of life, and see if I could not learn what it had to teach, and not, when I came to die, discover that I had not lived. I did not wish to live what was not life, living is so dear; nor did I wish to practise resignation, unless it was quite necessary. I wanted to live deep and suck out all the marrow of life, to live so sturdily and Spartan-like as to put to rout all that was not life, to cut a broad swath and shave close, to drive life into a corner, and reduce it to its lowest terms.” ― Henry David Thoreau