What I Learned About Myself by Taking the Long Way

Written by Kailee Smart

Kailee is an American-Italian photographer, writer, and traveler who fell in love with her roots and never looked back. She first lived in Rome as an au pair in 2019, an experience that changed everything. Since then, she’s explored over 50 cities and towns across Italy and now spends part of the year in her family’s home in the peaceful hills of Rieti. She currently lives in the UK, where she's working for charities, managing their socials. Deeply passionate about language, cultural connection, and soulful storytelling, Kailee shares honest reflections, travel tips, and glimpses of slow, intentional living around the world. Follow her journey at www.kaileesmart.com and use code KAILEE for $70 off your own RomeAbroad adventure.

28 April 2025

When I first started traveling, I wanted the safest option. The one with the map, the plan, the step-by-step. And honestly, that made sense at the time. But what no one tells you is that there’s a kind of magic that only happens when you don’t have it all figured out.

Last year, I drove from South Wales to central Italy. Not a flight, not a train,  just me, my partner, and a very packed car. We took the long way, slowly crossing through five countries, two mountain ranges, and more languages than I could speak fluently. We got lost, broke down in Switzerland, and spent the night in the attic of a French grandmother who didn’t speak a word of English. It was chaotic. It was slow. And it was one of the best experiences of my life.

Traveling by road gives you something different. You don’t just get there. You feel the shift. You watch the scenery change inch by inch. You get to sit with the journey, and in that space, you get to meet yourself.

And honestly, I wouldn’t have done any of this if I hadn’t been an au pair first.

That experience gave me so much more than a job abroad. It taught me how to trust myself. How to stay grounded in unfamiliar places. How to communicate even when I didn’t have all the words. How to be resourceful, adaptable, and curious, all things I carried with me into this journey. Since becoming an au pair, I’ve ridden mopeds through Chinese cities, biked through quiet Italian villages, and crossed Swiss lakes on boats when our car broke down. I’ve navigated new countries without knowing exactly what I was doing. And I’ve grown into someone who doesn’t just travel, I experience.

You don’t have to choose the hard route to grow. But there’s something powerful about traveling in a way that asks you to slow down, to pay attention, and to let go of the plan. That’s the kind of travel that changes you.

So if you’re thinking about taking a leap, whether that means becoming an au pair, exploring a country solo, or taking the long way through someplace new, here’s what I can tell you: you are more capable than you think. The road will meet you. The world will open up. And the version of you who comes home will be even more whole.

Because the best part of the journey isn’t just where you go. It’s who you become along the way.

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