Let’s talk about wrong turns, the kind that make you doubt every choice you made to get here.
I once followed a cat in Istanbul.
Not in a metaphorical sense.
A real cat.
It trotted down a narrow street, its tail flicking like it owned the whole city. I didn’t know where it was going. But I went along anyway, because why not?
Five minutes later, I was in a sleepy courtyard with old men playing backgammon. The air was thick with tea steam and laughter from the afternoon. One of them waved me over, probably because they thought it was funny that a stranger had come in after a street cat.
Amazon: Where Have I Been All My Life
That’s the thing about making a wrong turn: it gets you to the right place.
No one talks about the trip where everything went well.
The stories that are worth telling again?
The detours. The street signs that don’t match. The “this doesn’t look like our hotel” times.
When someone asks me about my most memorable trips, I don’t start with museums or famous places. I begin with the errors.
A woman once commented on one of my travel posts, sharing how my story about Istanbul reminded her of the time she unexpectedly found herself at a stranger’s wedding because she followed the music. It turned out to be the best night of her life.
That’s the power. That’s what aimless wandering feels like.
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3. Why Perfect Plans Kill Real Adventure
Let’s get this straight: planning isn’t the bad guy.
Planning too much is.
You know the type: color-coded tabs, spreadsheets, and bathroom breaks between “Visit museum” and “Buy souvenirs.” People who act like travel is a test they studied for.
Wanting things to go well is fine.
But here’s something no one tells you: if you plan every second, you won’t have time for the things that make travel truly memorable.
Embracing the unexpected moments and surprises during your travels can lead to some of the most memorable and meaningful experiences.
The unplanned.
They are somewhat disorganized.
Think back to your last trip. The strict schedule. The stress of “making the most of it.”
You probably saw more famous places than your heart could handle.
But did you sit still long enough to really feel the place?
I heard a couple arguing in Rome once. They were behind schedule for their next stop. The woman begged for five more minutes because “this street feels like magic.”
The man tapped his wristwatch.
He missed the magic.
Many people do.
A traveler wrote to me recently and said, “After reading your article about wandering, I left a whole afternoon open in Lisbon.” I found a bakery owned by a family that didn’t have a sign on the door. The best afternoon of my whole trip.
Sometimes the world only opens when you stop trying to control it.
4. The Joy of Being Exactly Where You Didn’t Want to Be
When you look around and think, “Well… this isn’t where I wanted to be,” you get a certain feeling.
It’s a mix of being a little scared and being in awe.
Like when I got off the train too early and ended up in the wrong Swiss village. At first, I was angry for ten minutes, but then an old man sweeping his porch waved me over and offered me homemade cider as if it were the most normal thing in the world.
I was there for an hour.
I didn’t even ask what the village was called.
Some things don’t need to be labeled.
When you are “somewhere else,” you let go of your grip on yourself. The list of things you need to do in your head gets less strict. Your personality finds room to stretch its wings and breathe freely in these unfamiliar territories.
You turn into a new person.
Or maybe just more you than usual.
People don’t talk about that enough.
5. Getting you to throw away the itinerary (a little)
I’m not saying to throw your phone into the ocean and go into the woods like a poetic disaster. But maybe, just maybe, leave one morning free on your next trip.
Let the city make the choice for you.
Walk until something catches your eye. A scent. A noise. A storefront that looks like it doesn’t belong in this decade. A line of people waiting for bread that goes around the corner (a good sign).
Let yourself go.
If the thought of not knowing where you’re going makes you sweat, start small. 20 minutes without looking at your phone. A street you’ve never walked down. A neighborhood you didn’t plan to visit.
Believe me, it’s worth it.
Everyone who has read it has told me the same thing: “I found something I didn’t even know I was looking for.”
If you want more stories like this, with more wandering, more human moments, and more travel that isn’t all shiny and new, Join us for more stories like this. Keep exploring. Subscribe now. Become a part of the small group of people who enjoy getting lost in a nice way.
The world unfolds in new and unexpected ways when you relinquish the need to dictate its course.
Are you ready to wander?
