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

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.

So that’s one part of the equation: I’ve seen the world, and I’ve connected with its citizens. It’s been really fun and I have some great yarns to share around the fire. For a person who likes to tell stories, that’s a smart investment. There’s a downside, though. It’s tough to bounce around the world for 15 years and still have your career progress in a linear way. It’s not a recipe for wealth. I do not own a home, I’ve never purchased a new car, and today I walked into a meeting in dress shoes that I bought 18 years ago. I’m dead certain that our publisher noticed the scuffs.

Putting passion over being comfortable means that you really will be less comfortable sometimes.

Vagabonding is not a life without worry. When I sailed through a chain of Indonesian islands and spent a week with Komodo dragons, I thought “this is the only way to live.” But when I came back home from a huge extended trip to find my friends getting married, talking about their investments, and starting families, I wondered if I’d missed the boat. What if I never got my act together in time to have a kid? What if I never stayed in one place long enough to make my creative dreams a reality? What if I missed the chance to find a soulmate?

It would be lazy to say that my way is right, and lazy to say that my way is wrong. My way is just “a way.” I’ve made the choices I’ve made and, for me, that’s made all the difference.

So let’s look back on that question implied by the headline: How do you know when you’re ready for the “trip of a lifetime?” Answer: you don’t. Being ready to embark on a big adventure is no different from being ready to raise a child, or move to Hollywood to chase your acting dreams, or start a food truck. The people who do these things never feel truly prepared. They just launch themselves into the abyss and sort out the details along the way.

Over and over we’ve seen this model proven out in The Mad Ones — a series about bold adventurers who were willing to cancel streaming data, stop buying rainbow donuts, and eventually quit their jobs. They’re 21st century brigands who find a particular value in long trips over packaged vacations. Time and again, the people we talk to argue that this type of travel builds a better, more broad-minded future for the planet. And I tend to agree (though there are plenty of other routes to the same goal).

Of course, it doesn’t always go that way. You might decide to go on a big trip and get mugged, or scammed, or die and long-term travel will cause at least a slight increase in danger on each of those counts. At some point, travel — like everything else in life — becomes a simple risk vs. reward calculation and not everyone wants the risk or values the reward. Some of the fears I’ve had as a result of choosing travel over a more natural career arc were silly, but some were on point. My friends really are set up better financially. My creative dreams were slowed down. I wasn’t imagining it.

When we posted about lifelong wanderer Christopher Many, this was one of the responses on Facebook:

“And when he finally decides to settle down he will be old and withered. And broke from having never held a steady job. His only shot in life is for his books to sell. Good luck on that.”

That’s a viewpoint steered by panic, but it also sounds a lot like the voice in my head at different times in my life.

In the end, if you push out of your comfort zone because of reading this post, and everything spirals out of control, I won’t have to deal with the repercussions. I’m just here to argue that travel deserves a place in your life the way our TV writers argue for the virtues of their favorite TV shows. You’re curating the life, we’re offering recommendations for things we love in hopes that you might love those things too. If you try it and don’t like it, it’s just like when you don’t like the TV show: you can always change your mind.

So when are you ready for “the trip of a lifetime?” Now. Or never. But hopefully now. Travel, like so many things in life, requires faith. Faith that your life is going to work out okay — that it might just be better because you decided to break your routine and see the world (or your country). That can be hard, especially in this era, when so many choices are sponsored  by fear™.

Nothing I write can quell those fears. Not completely. Facing them is part of what makes travel so invigorating in the first place. But I will say this: If you’re on the fence — wondering whether to jump blindly toward some grand adventure — I hope you’ll trust the universe and leap. I think you’ll end up glad you did.

Steve Bramucci is the managing editor of Uproxx Life. He can be found on Twitter and arguing about breakfast foods in the comments section.