How To Know When You’re Ready For The ‘Trip Of A Lifetime’

Editorial Director, Life
07.26.16 12 Comments

When I was 19, I dropped out of college to travel the country. The week before I left, my roommate’s mom leveled her eyes at me and said, “If you leave now, you’ll never get a degree.”

I left anyway. I hitchhiked, slept in bus depots, and cleaned dishes at restaurants in exchange for food. I sang chants with Trappist monks, spent two weeks on a weird hippy bus, and, when things got desperate, sold my blood for $40/pint. Every single day I felt raw and alive and “part of the world.” New smells, tastes, and ideas were entering my mind-space at a breakneck pace. I fell in love with the road and learned how to be lonely without being miserable.

After five months, I reenrolled and raced to catch up with my class. As it turns out, college isn’t going anywhere and Sallie Mae is happy to give you high-interest loans. My focus improved, my grades leveled up, and my appreciation for the degree I was going into debt to earn increased tenfold.

Fast forward. At 26, I quit my job to travel the world. I planned the trip for eight months and during that time I didn’t once buy a mixed drink or a six pack of beer. I drove a Honda Civic that cost $1,000, with no stereo or AC. I bought my clothes cheap and had them mended when they ripped. By the time I left, I had $24,000 in the bank — most of which I’d saved while getting paid $18/hr as a third grade teacher and making monthly payments on $46,000 worth of school loans.

During this second big trip, which ended up lasting 13 months in total, I dug a “well of experiences” — stories that have become integral to who I am. I bought a Nissan Patrol and bounced through East Africa, rowed a traditional Vietnamese x’ampan down the Mekong Delta, and trekked deep into the Australian outback with an Aboriginal elder and his family. I started to understand my place in the world and the philosophies that I hold dear began to take shape. With each new country, each experience, I was cobbling together a unifying theory of myself. In short: I became an adult.

After those two life-changing odysseys, there were smaller “big trips.” Three months crossing Australia in a car powered with used french fry oil, a summer bumming around the Cayman Islands, a spring spent in Amsterdam — plus dozens of travel writing trips that I extended on my own dime. Palestine. Barbuda. Colombia. Namibia. None of them was particularly well timed or planned with any sort of precision.

Along the way, I’ve met people and seen places and gathered a collection of moments that shaped me. But who hasn’t? You could say that with every bit as much validity if you never once left your home town. I wouldn’t dare suggest that there’s something objectively better about a life spent on the road. You can travel and still be a dick; you can stay home and become the coolest person on the planet. For me, the choice was to make my sample size of places seen, cultures shared, flavors tasted, and people met really, really broad. I think having this large sample size has brought me closer to the person I want to be, but that doesn’t necessarily mean that the universe is somehow cosmically better because I went camping in the Amazon basin.

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