How Travel Made Me Fluent in Uncertainty

I've learned to live with more questions than answers.

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Oaxaca, Mexico During Día De Muertos (Photo: Jon Santiago)

Scrolling through my Substack timeline last week, I came across a post from

Jill Amatt - Full-time Nomad

where she offered advice to people interested in becoming nomads. In particular, one line in her introduction grabbed my attention:

"You MUST take the leap even if you don't have all the answers. Once you get out into the world, you will realize that you are far more capable than you thought, and your confidence will soar."

It’s a sound piece of advice that applies beyond travel. After all, we’re really just winging it when it comes to life, making up the rules as we go.

That line plus the rest of her piece got me thinking about how travel has shaped my thinking around living better in general. I thought about the skills I’ve developed on the road and how they serve me no matter where I am.

1. Be Resourceful

Money matters, especially when you’re on the road. Whether you’re on sabbatical or working remotely as a digital nomad, you’ve got to learn how to stretch every dollar you have.

Traveling through Europe for the first time, I took this idea to heart. Instead of constantly splurging on hotels, hostels, or Airbnbs, one of the ways I saved money was by trading my skills as an English-speaker for stays in 3-star resorts.

The deal was this: spend several hours a day chatting with locals in Poland, Hungary, and Czechia who wanted an immersive experience. In return, you got free food, accommodation, and a memorable cultural exchange.

Three weeks of this saved me nearly a month’s worth of expenses, but the main benefit wasn’t solely financial.

Volunteer work like this taught me that our most valuable resource isn’t always our bank accounts. It’s actually things we take completely for granted, like our time or skills that come second nature to us.

2. Have a Plan, But Be Flexible

I’ve never been someone who likes to make rigid plans about my trips (or my life for that matter). But I’m also not one to fly totally by the seat of my pants, either.

You don’t have to make a binary choice between the two. Travel has taught me that there’s a sweet spot somewhere in the middle.

During my second trip to Europe in 2022, I planned a 5-day visit to Budapest. What I did during those days I left totally up to chance.

One night, I walked into a traditional Hungarian restaurant to have dinner by myself. Another guy, also on his own, asked me if I wanted to share a table since we were both in for a long wait.

As someone who appreciates random moments of serendipity like this, I said yes.

Over bowls of goulash, he shared with me why he was in Budapest. He’d chosen to flee Russia instead of fighting the war in Ukraine.

He left behind his family, lost his job, and saw his finances frozen thanks to sanctions. He had to convert most of his savings into crypto just to survive.

We may have been sharing a meal that night, but we didn’t share the same reality. I was in Europe by choice, free to return to the U.S. at any time. He was there because he has no country to go back to.

Meeting him was a reminder of how we often take stability, especially in America, for granted. We make long-term plans, assuming we’re in complete control of our future.

But the truth is, anything and everything can change in an instant.

3. Empathy Is Humbling

There are few experiences that humble you faster than being unable to express yourself in another language.

Most Americans don’t experience this, because we have the luxury of speaking English, the lingua franca of the world. But it’s a lonely feeling when you’re physically present, yet mentally elsewhere in the company of others.

I remember being in San Miguel de Allende, hanging out with my Mexican ex-girlfriend and meeting her friends for the first time. They laughed and reminisced, while I caught maybe every fifth or sixth word, my brain translating everything a beat too late.

I wanted to share my thoughts and feelings. I wanted to connect more than superficially.

But despite five years of Spanish classes as a teen and later 5 months living in Colombia as an adult, I still hesitated every time I opened my mouth.

Experiences like this make me think about immigrants to the U.S. who don’t speak any English. I think about how difficult it already is to build a new life abroad, combined with the struggle to express exactly who you are.

It must be isolating, vulnerable, crippling even. As someone who’s seen the other side as by traveling, I’m now familiar with those feelings.

What Ties Everything All Together

Travel teaches you how to be comfortable with the idea of not knowing what’s next.

When you think about it, everything that appears permanent is actually pretty fragile. Jobs, relationships, etc. - they’re all held together by looser threads than we’d like to admit.

But the skills you build through travel can help you thrive in an increasingly unpredictable world.

• Being resourceful gives you confidence you can figure things out in spite of your limits.

• Being adaptable helps you roll with the punches.

• Being empathetic reminds you there are people out there who’ve lived similar experiences, too.

Putting these skills into practice has helped me reframe how I view uncertainty. Rather than fearing the unknown, I remind myself there's an opportunity for something positive to happen instead.

As Jill said about a living nomadic life, you need to leap without having all the answers. It’s scary, but the journey will show you what you’re capable of. That’s the kind of souvenir I want to hold onto.