Taking a Hooky Day

I took a hooky day into New York City last week — spurred by the necessity of picking up my new glasses with my first pair of progressive lenses, but I’m not going to trek the whole way to the Upper West Side just to run an errand and come home.

There needs to be a little bit of fun involved if I’m taking that trip. So I chose to make it a hooky day, and if you’re not familiar with the concept, I thought it would be a good time to fully spell out what I mean.

I first wrote about taking an art hooky day back in 2023, so it’s definitely worth revisiting. In that post, I said:

Even if you haven’t read Julia Cameron’s The Artist’s Way, I bet you’d know what I meant if I talked about an “artist’s date.” That’s what she calls them — a monthly appointment with oneself to do some sort of creative activity — but I’ve been referring to them as “hooky days” ever since I started working on my own and didn’t have The Man to answer to for my productivity.

That single paragraph encapsulates the hooky day in a nutshell, but let’s break it down.

Hooky Day Rules

Make it a standing appointment.

Ideally, you would want to set aside one day a month for a hooky day, but I’m not going to dictate a specific time frame. Creativity doesn’t work on a schedule, so why should hooky days?

My hooky days don’t follow a set schedule, but I do make it a point to get one on the calendar every quarter. If you have a Notion dashboard like my monthly review dashboard, you can even create a running list of hooky day ideas.

Make it a date with yourself.

I feel very strongly about doing hooky days by yourself. When you bring another person along, it’s more of an Adventure Day, and you’re always managing someone else’s desires and expectations and timelines along with your own — no matter how in sync with them you might be.

When you’re having a solo hooky day, you’re on your own schedule. You decide exclusively what you want to see and do and eat and experience.

Make it fun.

This, of course, is one of my main life tenets, so it obviously applies here. Pick your own idea of fun!

Even though I often refer to these adventures as “art hooky days,” it doesn’t have to involve art or a museum. That’s just where I frequently end up, since there’s a lot I’m interested in seeing on my own time — and I usually abandon the people I’m with at museums to go at my own pace anyway.

It can be as simple as treating yourself to lunch at a place no one else wants to go with you. This is a big one for me because food always has to be involved and I married a picky more selective eater. A date with a bowl of clams is always a good date.

Going hiking, kayaking, on a long walk, or any way you like to spend time outside can be a hooky day. On one of my hooky days, I decided I was going to re-read The Great Gatsby in Central Park and since 2025 is the centennial of the book’s publication, the time is right to do that again!

A hooky day can involve seeing a much-anticipated movie in the theater, if that’s your thing. Or live theater — which might take a little more planning, or you can see what tickets are available the day before or day of. Or you can create your own live performance if you have a ukulele and a dream.

Which is what I did on my latest hooky day: I went back to Central Park and played on a bench for an hour, then recorded a song for an upcoming installment of the Ukulele Alphabet. After picking up my glasses, I treated myself to Filipino food and then a two-flavor cup of sour cherries and cream AND strawberry shortcake ice cream at Van Leeuwen.

By that time, I was ready to be on the 3:00 pm train back to the suburbs, and it was a perfect spring adventure.