Surprise Me

Breaking free from the algorithm is kinda nice.

Some of my favorite discoveries didn’t come from plans, algorithms, or five-star reviews. They came from wandering, wondering, and paying attention (sometimes in the form of eavesdropping on strangers’ conversations).

I didn’t plan to learn about txakoli wine. But one thing led to another, and suddenly I was deep in the internet rabbit hole of Basque winemaking like it was my new life’s calling.

My txakoli deep dive happened online, but it was sparked irl, at our neighborhood wine shop. And not in the usual way, either. Normally, I pick up a bottle and get curious about something on the label. This time, we were just browsing, trying to decide what wines to keep on hand for when people come over, when R turned to me and asked, “Should we pick something up for Chuckly?” (“Chuckly” is a nickname he uses when someone is annoying but lovable — sometimes even for our dog.)

The wine store clerk overheard his question and said, “We have both red and white Chuckly!”

… what?

She gestured to the shelf, and I saw it: txakoli. Both red and white. Txakoli is pronounced, you guessed it: Chuckly. 

That moment didn’t come from a color-coded to-do list or an Instagram recommendation. It came from being out in the world, living life and paying attention.

We live in a world that is very online. Algorithmic and curated, designed to show us exactly what we want — before we even know we want it. Or at least, what the internet thinks we want. Personalized newsfeeds, curated playlists, autofill email responses, targeted ads that make you feel certain your phone is always listening.

But sometimes, you don’t know what you want until it surprises you. And the algorithms don’t leave a lot of room for surprise.

Some of my favorite memories didn’t come from a color-coded travel spreadsheet or hours of research of “what to do in [insert destination here]”. They came from wandering, from overhearing, from being open to adventure. Some of them are:

• We met our now-close friends in a random shoe store we wandered into in Florence.
• We found an amazing off-the-tourist-beaten-path cocktail bar in Maui after overhearing some locals talking about it.
• We ended up in a tiny sushi restaurant in Tokyo, with no reservations and no plan, having a private dining experience with two friendly regulars who turned dinner into a whole experience.
• I found my ceramics studio after chatting with someone at a local pottery pop-up.

None of those things would’ve happened if we had stuck to the plan (or had a plan in the first place). So how do we un-curate our lives a little and leave room for moments like these?

We spend a lot of energy trying to optimize our time: Get in, get out, get the best version, maximize the moment. It often, at least for me, ends up in analysis paralysis and/or decision fatigue. But sometimes the most memorable parts of life are the ones you couldn’t have scheduled if you tried.

So I’ve been trying to… try less. Here’s what that looks like for me:

Leaving room at the edges. Not filling every block of time with a task (it’s been a hard habit to break). Letting there be gaps and wiggle room. Space to breathe, to wander, to see where the day wants to take me.

Saying yes to small talk. Even if it’s awkward or boring, because sometimes a casual chat with a stranger in an elevator or a grocery store aisle or a random shoe store in Italy… turns into a whole story later.

Taking a risk and going off script. Trying the new spot with only five reviews, picking the unfamiliar bottle of wine, asking a human instead of Google for a recommendation.

Stay curious. Letting a question linger instead of immediately Googling it. Guessing, wondering, asking someone nearby. It’s harder than it sounds when the internet is in my pocket.

I’m not anti-algorithm. I like when Apple Music plays a throwback I forgot I loved. I appreciate a well-targeted restaurant rec. There’s comfort in seeing familiar faces on my feed. But I think it’s healthy to pop the bubble once in a while.

If all we ever see is more of what we already like, we could start mistaking the algorithm for the whole world. We start to think we already know what’s out there. We miss the strange, the funny, the offbeat, the oddly specific. We miss what’s just beyond the edges of the algorithm.

What if we stopped trying to optimize every experience and let some of them simply unfold? What if we got comfortable not knowing exactly where we’re going, or how long it’ll take, or whether it’ll be worth it? (This goes against my Type A tendencies, but your girl is trying!)

Because sometimes, the worth is in the wondering… or the wandering. The next delightful thing might not be trending, might not have thousands of reviews, might not even be on the map… but it might be just around the corner. You just have to be a little more open and little more willing to be surprised. And maybe you’ll end up buying txakoli for Chuckly.