Learning from the trip-ups on the trip of a lifetime

Feather Publishing
James Wilson

It was 10 years ago exactly that I took the trip of my life. Two of my friends, Brett and Lindsay, took off with me on a year-long trip that took us to 25 countries and six continents. We were young, reckless and ready for anything: the perfect combination for a year of shenanigans.

Since it was exactly 10 years ago, I’ve been going through my old emails recently and reading about what we were up to 10 years ago from the day, each day. Ten years ago from the day of writing this, for example, I was picking fruit on an orchard in New Zealand. 

I never kept a journal, so reading old emails I saved is the closest I can come to reliving the adventure. When reading these emails, one thought keeps resurfacing in my mind: I was an idiot.

I saved only a little over $1,000 to take with me for the year, so I worked in several countries along the way to pay for food, shelter and transportation to the next place. Picking fruit in New Zealand was one of the jobs I picked up on the way.

My friends and I got ourselves in sketchy situations with a carpe diem attitude that I would not want to relive. Re-reading these letters I wrote just brings one boneheaded mistake after another to mind. At the time, however, they seemed like good ideas.

That job on the orchard, for example, ended quickly as I got into an apricot throwing fight with one of the other workers. Our boss turned the corner and one of my apricots went sailing into his face, breaking his glasses.

In Argentina, Brett and I were kicked out of a lodge because, somehow, we managed to make too much noise playing chess. Now that I think back to it, the liter-sized bottles of beer may have contributed to that.

Brett and I also had the majority of our stuff stolen in Costa Rica because we wanted to save a few bucks and stay at some shady motel.

I got attacked by a bunch of street performers in Italy for trying to encroach on their territory. That was quite the sight: living statues, robots and mimes all coming at me at once.

And as a topper, my idiot younger self spent a short amount of time in the jails of Australia, Vietnam and Italy. Don’t ask. Way too long of a story for each one.

There’s no denying it. I was an idiot. And I’m sure that 10 years from now when I look back to today, I’ll think I’m an idiot now. But despite the idiocy, that trip was an experience I wouldn’t trade for anything. I wouldn’t do it again, but I’m glad I did it then.

In addition to all the stupid situations we got ourselves into, we also had some truly amazing experiences. Some of the experiences were smaller and more personal and some were truly spectacular and grandiose.

On a personal level, meeting family in Australia and Israel was one of my highlights. The family in the United States and overseas had kind of lost contact with each other through the years and my showing up helped rekindle our connection.

Another personal victory I had was getting to know my friends I traveled with as well as I do. We all thought we knew each other before we embarked on the trip, but we were wrong. After being around someone literally 24 hours a day for a year, you get a whole new appreciation (or lack thereof) for that person.

There were so many countless introverted moments that will stay with me forever: introducing a Cambodian monk to The Beatles, trying foods I couldn’t pronounce let alone recognize, taking in views that stop the thought process and living on and for the essentials of life.

I learned as much that year from my mistakes as I did from my personal victories. Ten years later, I can look back and see how different I am now than I was then, but I wouldn’t be if I hadn’t taken that trip.

Somehow, unbeknownst to me then and through all the shenanigans, I managed to gather some memories that will be cemented in me until the day I die.

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