Halloween is perhaps my favorite collective civic ritual of the year. At least here in Brooklyn, it’s the night everyone steps outside and hangs out. People decorate their stoops with ghouls and witches and bats and spiders. Neighbors hand out candy to strangers (and they accept them). We carve meaning into pumpkins and tell stories through costumes. There is shared context on the street – K Pop Demon Hunter! Charizard! Bernie Sanders! It’s chaotic, participatory, and delightfully collective. For one night, we agree – across difference – to play and be silly and mischievous together.
Last week, I wrote about how and why some of the best gatherings start as jokes. And this past Monday, I sat down with Austin Kleon, author of Steal Like an Artist and one of my favorite newsletters on Substack, for a live conversation about creativity, humor and why so many creative breakthroughs start as jokes and by just “messing around.”
Austin said something I can’t stop thinking about: “It’s always Halloween for the artist… Costumes and props are very important because they help us get into the spirit.” (He showed up, appropriately, in his artist smock (his own version of a costume) complete with a (fake) pencil cigarette.)
Artists and gatherers create temporary, alternative worlds. And, it turns out that when we start with just “tooling around,” or with a tongue-in-cheek comment and then pursue it, it often leads to deeply hilarious collective experiences. Some of the most powerful gatherings I’ve seen begin this way. A church healing division by literally dunking its deacon. A group of worn-out moms who declared: if you talk about your kids, you take a tequila shot. Each started as a joke. And then developed a life of its own.
When’s the last time you let yourself just mess around — and what came of it?
As always,
Priya
