The Playful Path: Letting Go of Rules to Jump Higher

I’ve noticed how easy it is for my practice with meditation to become... rigid. What once opened me up has, at times, felt like a cage I built to stay “on track.” A militant mindset can sneak in under the guise of discipline. But what if there’s another way?

Recently, I began experimenting with something playful to help with my approach to and relationship with meditation.

I took two bowls.

In one, I dropped slips of paper with different numbers: 5, 6, 7, 8, 10, 11, 12. In the other, my top 7 guided meditations.

Each day, I pull one from each bowl. One gives me the length of time. The other gives me the meditation.

It sounds simple, maybe even silly. But this has been one of the most liberating things I’ve done in a while.

I used to always listen to guided meditations from start to finish. That was the “correct” way. But, when a 21-minute meditation got paired with a 12-minute time limit, something had to give. So, I started playing. I’d begin a meditation 9 minutes in.

At first, it felt weird. Like walking into a basketball game already in the second quarter. But I reminded myself: I’m here to play.

Playing has no rules. As I wrote in, “From the Search to the Play,” kids don’t ask, “am I playing correctly?” They just play.

It felt awkward at first. That old programming kicked in: “Finish what you start,” “start from the beginning.” But I stuck with it. And strangely enough, it was healing. I’d get up from these little mismatched sessions feeling lighter. Even tension in my neck and head began to melt away.

It hit me: This whole journey with meditation—years of inner work—has really been about learning to flow and play with life. And now, I’m seeing how meditation, once my tool for liberation, had become another structure. A structure I needed to outgrow so I could play again.

This reminded me of something my coach shared with me about Pesach Sheini, the “Second Passover,” observed on the 14th of Iyar (the day after my Hebrew birthday). Unlike the first Passover, Pesach Sheini doesn’t begin with a search. No hunt for chametz. It just is.

The Torah tells us it’s for those who missed the first one; a built-in second chance. A cosmic reminder that it’s never too late. In Chassidic thought, Pesach Sheini even draws a greater divine flow than the first. Like a trampoline that helps you jump higher than you ever could on your own. You don’t climb steps, you leap. You skip the linear process.

Maybe that’s what my two bowls were offering me: a jump, a spontaneous gateway into something richer, lighter, freer.

No search. No prep. Just... play.

It feels like starting a book from the middle. But who says you can’t? The rules are the ones we agree to. I’m starting to agree to something new.

Some days, life doesn’t begin at 6 a.m. Maybe it starts 20 minutes before your first meeting. Maybe you missed your “ideal” start. But, that doesn’t mean the day’s lost. You can still choose how you show up.

That’s what play is. It’s reclaiming the moment.

It’s letting go of the script.

It’s saying yes to spontaneity, and no to shame.

It’s starting exactly where you are.

And it’s remembering, even in the middle of things you can always begin.