Chasing Maybe
Why I shouldn’t be left unsupervised
Ever since I was young, I’ve loved getting lost.
Not the alarming kind of lost. Not the kind that ends with someone calling your name through a megaphone. I mean the gentle kind, where you take one wrong turn and suddenly the day stops being a schedule and starts being an adventure.
Rani has never fully trusted this quality in me.
She has a theory that, despite all available evidence to the contrary, I am occasionally still thirteen years old and require supervision. In her view, adulthood involves things like sunscreen, water, vitamins, and a basic awareness of where you are and why you are there.
In my view, adulthood occasionally involves ignoring all of that.
On this particular day, Rani was a conference in Hong Kong where I joined her. She went off to work, and I woke up in the hotel with the dangerous freedom of having no plan at all. When that happens, my mind immediately returns to its natural state, which is somewhere around middle school.
What should I do today?
So I walked in the general direction of the ferry terminal.
I had no reason to go there. I just liked the idea of ferries. Ferries suggest movement, and movement suggests possibility, which is usually enough for me.
When I arrived, I saw a line of people buying tickets. I had no idea where they were going. I didn’t know how long the trip was, what was on the other side, or whether I would understand a single sign when I got there.
Which reminded me of another time I saw a line of people and decided that was reason enough to join it.
Years ago, I was in the Castro district in San Francisco and noticed a long line outside a movie theater. The crowd was an unusual mix — people in elaborate drag, families with small children, and several people dressed in costumes that suggested this was not going to be a normal afternoon at the movies.
I had no idea what was playing.
I didn’t ask.
I just thought, whatever this is, it’s going to be fascinating, and I would very much like to be part of it.
So I bought a ticket.
It turned out to be a Little Mermaid sing-along.
Which was all fun and games until the lyrics appeared on the screen and the entire theater enthusiastically committed to full participation, at which point I found myself standing in the aisle of the movie theater, surrounded by strangers in wigs and sequins, being gently but firmly encouraged to sing along to “Under the Sea.”
This is the kind of thing that happens when you decide you don’t need to know where the line is going before you get in it.
Standing at the ferry terminal in Hong Kong, watching people buy tickets to a place I had never heard of, I had exactly the same feeling.
Naturally, I bought a ticket.
Forty-five minutes later I stepped off the ferry onto an island called Cheung Chau, just off the coast of Hong Kong, wondering how I had managed to turn breakfast into international exploration.
At that point I decided to follow the philosophy of the movie Yes Man, which, as far as I remember, is about what happens when you stop pretending you have control over your life and just start agreeing to things.
The first thing I saw was a small dim sum restaurant right on the water. I hadn’t planned on eating, but planning had clearly lost its authority over the day.
So I said yes.
It was fantastic, which immediately encouraged me to continue making poor but interesting decisions.
A little further down the street I saw a tiny bike rental shop run by two people who spoke almost no English. They pointed at the bicycles and smiled in a way that suggested this was either a good idea or a terrible one.
I had not seen the island.
I did not know how big it was.
I did not know how long it would take to ride around it.
So I said yes again.
Soon I was riding along a narrow road that curved around the coastline, the sea on one side, green hills on the other, thinking about how this was not at all what Rani meant when she said, “Have a relaxing day.”
Every few minutes there was another sign pointing toward something — a shrine, a temple, a cave, a path that seemed to go nowhere in particular.
Each time, I stopped.
Each time, I said yes.
One sign led up a steep path to a shrine overlooking the water. I left the bike at the bottom and climbed for ten minutes until the view opened up over the coastline in a way that made the whole island feel suddenly unreal.
Another sign pointed toward a cave. The cave itself, if I’m being honest, was not particularly impressive, but the walk to it was extraordinary — a long, quiet stretch of coastline where I passed almost no one at all.
It was hard to believe that only a few hours earlier I had woken up in a hotel room in the middle of Hong Kong wondering what to do with the day.
Now I was alone on an island I hadn’t planned to visit, riding a bicycle I hadn’t planned to rent, looking at places I hadn’t known existed.
This is what I’ve always loved about getting lost.
When you know exactly where you’re going, the day becomes something you move through in order to arrive to an expectation you already had.
But when you don’t know where you’re going, the day becomes the destination.
That evening, when Rani came home, I told her about the ferry, the island, the bike, the shrine, the cave, and the fact that I had spent most of the day wandering around without a map, a plan, or, as she quickly confirmed, enough water.
She listened quietly and then asked the questions she always asks.
“Did you wear sunscreen?”
“No.”
“Did you drink enough water?”
“I think so.”
“Did you take your vitamins?”
I hadn’t.
She shook her head the way someone does when they realize they are married to a person who cannot be left alone for too long.
She says I’m still a little kid.
And she may not be entirely wrong.
But every now and then, if you let the thirteen-year-old decide what to do with the day, you end up somewhere you never would have found on purpose.












I think that 13 year old you is my favorite version. What a great adventure!!
Great story, Andy. My husband is now a fan of your Substack, and we both loved this story as this is how we roll (but I bring the sunscreen).