(This is the final post in an eight-part series about my cross-country road trip from New York to Oregon. You can find the rest of the series here.)
My hitchhiking trip is over — but in a way, I’m still on the road.
Going to Portland was a break with the settled life I was leading before the summer of 2010. I’d lived in upstate New York for 23 years: born in Poughkeepsie, raised in Binghamton, educated in Ithaca. My whole existence occupied a sphere of about 200 miles. I traveled, but my mailbox was always in that same bubble.
Not anymore.
I’m back in Binghamton for the time being, but I’m not staying for long. No way am I settling here. Soon I’ll be moving — probably to Denver, possibly to Chicago, maybe to some other place I haven’t yet considered — and moving again after that. South America, Sweden, Istanbul, Dharamsala… there are a lot of lives to live in a lot of other places. Portland was just the first stop on an extended itinerary that may well stretch on for years.
It seems like a lot of people in my generation are on the same kind of open-ended ticket. Most people probably aren’t afflicted with a globe-tripping addiction like mine, but nobody — nobody — I know seems sure where they’ll be in the next two years. For those of us who tumbled out of college and weren’t handed a career with our diploma, the next destination is wherever they’ll hire us, wherever the rent’s cheap, away from our family’s basement — anywhere, anywhere but here. We all seem to be throwing darts at a map one way or another.
But that’s too grim a picture. In my first post of this series, I wrote a lot about that almost desperate uncertainty keeping my generation from settling down — which is not to be ignored, but also shouldn’t be the main reason. A better reason to postpone settling down is the sheer wealth of opportunities that living in a virtually globalized society gives us. We don’t have to settle for selling shoes in our hometown just because it’s the best job in 100 miles: with the Internet, we can find jobs on five continents, selling shoes or otherwise, without having to do so much as put on pants.
My trip, if anything, was a small-scale exercise in the travel opportunities technology has given us. Think about it: if I’d done the same trip ten years ago, I would’ve been taking a lot more on faith. I would’ve walked blind into almost every city I stopped in. The simple fact that I knew where I was going to sleep most nights, courtesy of CouchSurfing, took a great deal of risk out of the experience. The Internet allowed me to get information and make connections that I otherwise wouldn’t have had available, minimizing uncertainty, leaving less up to chance — which, in the end, considerably reduced the risks I took. Ten years ago my trip would’ve been an arduous series of best guesses and Hail Marys; instead it amounted to a pleasant stroll across the country to visit friends I’d already met. I might not have taken the chance otherwise, missing out on a wealth of experiences and perspective.
So it was with my trip, and so it is with life in general. Our opportunities are no longer limited to a single town, a single state, or, hell, a single country. We can make connections and open doors all over the world. We can build whole lives for ourselves in places we’ve never been while we sit in our pajamas.
I feel like I’m rambling. Am I rambling? There was a point I was trying to make…
Right, yes. So.
For my own part, I’ve wanted to explore long-term travel for as long as I can remember — since I was 11 years old, if not younger. This trip was intended as an initial test-run of whether I could do it. Now that I know that an unsettled life is not only realistic, but in a lot of ways easy, it’s almost impossible for me not to pursue it while I can. That’s where I’m headed now.
I realize that pulling stakes and resettling over and over might not be everybody’s slice of pie. But for the people in my generation who are agonizing about what they’re going to do with their lives, the news is still good: we’re living in a globalized society. We have the tools to make connections around the world. That gives us access to a wealth of options — both in our own country and every other. We can be successful doing any number of things in any number of places. All we have to do is pick one.
I’ll see you on the road.

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