There was a point, a lot of miles down a Uruguayan dirt road, where I started to question my decision-making skills. Jorge, a neighbor of a friend’s father, had offered to show us around and take us home for lunch. Home was supposedly on a vineyard.

We hopped in the back of his Jeep and headed out of town. He didn’t really speak English, but he seemed friendly. It had seemed like a good idea in town, but now, whipping down a road in the middle of nowhere, not sure of where we were, or who exactly this guy was, I wasn’t so positive.

Every good adventure has a point where it feels like a very bad idea -- that moment where you gut check and ask yourself, “If things start to go south, is there a way to get out of this?” I think you need that. If you felt comfortable all the time, you wouldn’t be getting anywhere new.


Speak up. Because you might end up somewhere awesome like this. Photo: Courtesy of Richard Bowden/Shutterstock

Trust doesn’t come naturally to me. Maybe it’s because I’m from New England, where we’re not always forthcoming, but I’m perennially skeptical of people I don’t know.

I’ve had to get over that to travel. Being in weird places full of strangers has shaken me loose of that a little bit. I am more likely to engage when I’m on the road, in part because you have to when you’re somewhere new and don’t know the lay of the land.

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Or maybe you don’t have to. There are plenty of people who plan out every step of their trips, who don’t ask questions or go with the flow. But I think leaving some things up to chance leaves room for some serendipity.

I’m not saying you should hop into any random dude’s car, or that you should willfully endanger yourself; I’m just saying that sometimes it pays off to be less skeptical.

Your vibe attracts your tribe. Go on ... don’t be shy. Photo: Jens Johnsson/Unsplash

Some of the best places I’ve ever been, I never would have seen if it weren’t for a stranger’s friendliness. I’m not hyperbolizing. By being just a smidge more trusting than I am in my everyday life I’ve ended up on a Marae in New Zealand, in the middle of Jorge’s vineyard in Uruguay and in a hidden A-frame cabin in Washington.

Traveling makes me say yes, and because of that I’ve had my eyes opened to the ways that other people live and been able to imagine what their lives are like. Which, I think, is why we travel in the first place. That’s part of the adventure -- glimpsing into a totally different life for a while, even if it feels a little scary.

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Usually, things turn out pretty well. Jorge gave us wine from his grapes and huge steaks, and his dogs loped around the yard in front of us as we had lunch. Looking out over the vineyard, not entirely sure of how we were going to get home, I was still sure I’d made the right choice.