Head Over Heels for the Itinerary. Head Over Heels for Abandoning It.

I love getting lost. Genuinely, literally, with my whole heart. There is nothing quite like the feeling of being somewhere new with no idea where you are and nowhere you have to be. Just you, the city, and the intoxicating freedom of having no one expect you anywhere.

Which is hilarious. Because I am also a deeply obsessive planner.

Color-coded itinerary, pins and notes for each attraction on a premade map, best times to visit each site. I know which museum closes on Mondays. I have the offline map. I have a backup plan for the backup plan.

And then I arrive somewhere. And the place has its own ideas.

I fall in love with places the way you fall in love with people. Helplessly. Inconveniently. Usually at the worst possible moment, when you had somewhere else to be.

In Hokkaido, Japan, we had done everything right. Packed itinerary, rented car, a list of points to hit and roughly how long each one would take. We were ready.

And then we started driving. The landscape was so breathtakingly beautiful, like we'd driven into a painting we didn't know existed, that we ditched the list entirely.

We stumbled into a village tucked into the woods that felt like it had been conjured from a dream- timber cottages, little workshops nestled between the trees, the whole place built upward and inward like the forest had decided to become a town. It was Fortree City in real life. We wandered deep into the village in complete, delighted silence.

And then it started raining caterpillars.

That's not a typo. We watched them fall from the trees, then spotted a woman in what looked like a hazmat suit, wielding a wand and flinging caterpillars away from the village. Other locals had their umbrellas open to repel them and gestured for us to do the same.

I turned to the hazmat suit woman and asked in Japanese: "Is it always like this?"

She responded, utterly unfazed: "It'll be like this for a few weeks. It's a seasonal occurrence."

We hightailed it out of there completely losing it- half horrified, half in hysterics- in a moment so absurd and so alive that no itinerary in the world could have planned it. The village itself was already surreal. The caterpillars raining from the trees while we chatted with a local in a hazmat suit was just the universe making sure we'd never forget it.

That is the feeling I'm talking about. That particular cocktail of wonder and chaos that only happens when you've fully let go of where you were supposed to be.

And that feeling... my god, there is nothing like it.

When you embrace being lost, you are the most free you will ever be. Freedom isn't the absence of plans- it's the moment you stop being held hostage by them.

Your eyes work differently. You actually see the road instead of using it as a corridor to somewhere else. The conversation meanders and breathes. Nothing exists except right here- this road, this person, this moment that nobody planned and nobody is rushing to finish.

The monuments are the reason you show up. The moments are the reason you remember.

And you can't plan the moments. What I've learned, after years of showing up to places with an spreadsheet, is that the things that change you don't live on the itinerary. They find you when you wander, when you choose a moments over a plan, and when everything goes sideways and you roll with it anyway.

In Vilnius, Lithuania, I had planned a sunset hike to the best viewpoint in the city. But during our Soviet history walking tour, we met a Mongolian-American woman who lived in Switzerland and worked for the UN. She's one of those people whose life is so fascinating you can't quite believe she's real.

We grabbed drinks after the tour and just... kept going. She opened up a whole world we knew nothing about: expat life, Mongolian customs and traditions, the kind of travels that make you reconsider everything you thought you knew about the size of the world. We spent the entire evening completely captivated by her stories, her perspectives, her reflections.

We missed the sunset. We missed the viewpoint. But we gained one of the best memories of the entire trip.

In Granada, Spain, we got lost looking for our Airbnb, luggage and all, wandering streets that all looked identical. We ducked into an ice cream shop for directions. Two French owners drew us a map by hand and walked us partway down the street.

We came back afterward to thank them and ended up staying for their whole story. We listened to why a scientist and a fashion designer left Paris to make ice cream in Granada, and what they thought of the life they'd traded for it. On our last morning, they invited us behind the counter and showed us how ice cream is actually made. I had never seen it before. I haven't since.

We never would have met them if we hadn't been hopelessly, completely lost.

In Sintra, Portugal, I forgot my mask. They were mandatory everywhere in 2022. It was 6am, nothing was open, and I stumbled around cobblestone streets feeling like an idiot. I spotted a cook on a cigarette break, deployed my most ambitious Portuguese and expressive charades, and somehow asked where I could buy a mask.

He gave me a pointed look, gently corrected my awful Portuguese, glanced at his watch, and chuckled. Then he disappeared inside and came back out not with directions, but with his entire box of masks. I reached for one. He gestured at the whole box. Take more. Make sure you're covered.

Forgetting my mask was what introduced me to Portuguese kindness.

In Tallinn, Estonia, the palace we planned to visit was closed. So we walked to the old town hall instead, which was also closed, hosting a classical concert. Feeling spontaneous, we bought tickets. Multiple musicians took the stage, each one better than the last.

And then the pianist walked out, and I lost my mind a little. I had grown up with him in California. Played music alongside him for nine years before life carried us in different directions. I hadn't seen him in a decade. And there he was, on a stage in Estonia, in a concert hall we only entered because a door we planned to walk through was locked. We were invited backstage during intermission, met all the performers, and I spent the rest of the evening catching up with an old friend I never expected to find.

Some of the most memorable things in my life didn't happen because everything went right. They happened because something went wrong and I YOLOed.

I give my whole heart to the plan. And then I give my whole heart to abandoning it. The reason I have a plan is so that I have permission to let it go.

Falling in love with a place requires the same thing falling in love with a person does. You have to stop trying to control the outcome long enough to let something real happen.

So I'll keep making the spreadsheet. And then I'll show up with my whole chest and let the place sweep me off my feet. I'll follow the road that looks interesting. I'll stand in doorways I wasn't supposed to find. And when something goes wrong — when I'm lost, when the door I came for is locked, when it's raining caterpillars — I'll YOLO. Because I know by now what lives on the other side of that.

Because the best parts of every place I've been weren't on the map.

They were the moments I almost missed because I had one.