The Freedom of Foolishness

The other night, my son asked me something that made me think: He asked me: “Why aren’t adults fun anymore?”

He’s right. Somewhere along the way, we traded play for purpose, laughter for seriousness, imagination for identity. We started dressing up not just for Halloween, but for life, wearing masks of respectability, titles, personas. And we forgot that behind the mask, we are still children of the cosmos, meant to play.

Halloween, at its root, began as the Celtic festival of Samhain, when the harvest ended, winter began, and the veil between worlds grew thin. People wore disguises to protect themselves from wandering spirits. But over time, the disguise became play the mask became ritual.

This year for Halloween I’m choosing the Fool. Because the Fool is dangerous. The Fool doesn’t protect an image, it has no crown, no crown to polish, no robes to guard, no followers to impress. The Fool dances barefoot in the firelight, laughs when others frown, speaks when silence feels safer. And the Fool cannot be trapped by projections of others.

There is a story I want to share. Once, Confucius was traveling with his disciples when they encountered a wild old man laughing under a tree. Curious, Confucius asked him about the Way. The madman only stuck out his tongue, made silly faces, and roared with laughter. Confucius grew offended and demanded, “Do you know who I am?” The madman smiled and said, “I know who you are. I know that you know who you are. But that is exactly why you don’t know what you are.”

The disciples were shocked, but Confucius grew quiet. He finally admitted: “This man is beyond me. He is free.” Sometimes, to step into truth, you must first pass through nonsense. Sometimes, wisdom hides behind foolishness.

This year, Halloween I invite you to experience the Halloween as an initiation. A chance to strip down from everything you built yourself to be: the serious roles, the careful images, the heavy masks. To remember what freedom feels like when you let yourself be ridiculous, unpolished, unprotected.

I’ll be the Fool, because I need it. Because even as a spiritual guide, I need to break free of the expectations others place on me and the ones I secretly put on myself. I need to laugh at my own seriousness, stumble, dance, and play.

So this Halloween is here so you can forget the character you’ve been playing, and let yourself be the Fool. Laugh too loud. Wear something outrageous. Say something foolish. Break the spell of who you think you have to be, because sometimes, the greatest wisdom is hidden simply in foolishness and ability to laugh at yourself.

Remember, If you are certain of who you are, you have not yet touched the mystery of what you are.