Once upon a time…
I stumbled on an open mic night at a Mexican restaurant in Williamsburg. The performance was behind an unmarked door at the end of a long, dark hallway lit only by black-lights that illuminated the skeletons painted on the walls.
Honestly, I only found it because I was looking for the bathroom. Finding both restroom doors locked, I noticed a third door at the end of the hall and decided to try it. My curiosity, as always, getting the best of me.
The light in my face as I opened the door was jarring and made me squint. The room behind Door #3 was bright and cold to the point of feeling sterile. It was haphazardly furnished with benches facing a microphone centered on the far end of the room. To my left and right along the wall looked like storage for the bar.
There couldn’t have been more than 20 people in the room, most standing at the back and one at the mic. I felt like I’d entered a meeting I wasn’t invited to.
🙅♀️ Not in the mood for a story? Go straight to this week’s episode about creativity and play.
Only I was warmly, yet quietly, welcomed into the room with smiles and nods to sit down by what I quickly learned was a room full of comedians practicing their standup routines. And I got a front row seat.
At first I felt lucky. I’d finally found my first underground event, thus earning me a New York insider badge that I’d long been seeking. Only instead of talented comedy hopefuls, I’d found a room of rejects.
The routines were terrible. The roughest of the rough. Even the most polished comedian failed to get more than a chuckle from their peers (or me). The majority of them leaned on mainstream themes like sex, violence and mommy issues without originality.
“We’re all painted birds, freaks with our own eccentric coloring, and wherever we fly, the unpainted birds peck at us and drag us to the ground,” Gabriela tells Anya. “Then we’ll disguise our feathers,” Anya responds but Gabriela is unimpressed: “And be like every other unpainted bird? Thank you, Auntie, but I’ll keep my color.” - Life as Fiction
Every once in a while, though, a comedian would produce an inkling of a funny joke. A phrase that triggered an unforced laugh from the small audience. Still, those who did achieve traction with their joke ultimately botched it. They followed through in the wrong way or ended up going down the wrong path altogether.
But...there was something there. And what was most interesting to me is that none of them seemed plussed by their blunders. Neither did the audience. It was as if they were playing a game together, and I was watching from the periphery.
It reminded me of this book: Finite and Infinite Games. Finite games are played for the sake of ending them, but infinite games are played simply for the sake of playing. Infinite games don’t end - the whole point is to continue playing the game forever.
These comedians, they didn’t care if their jokes didn’t work. To them, it was information, brainstorming, testing. They were in a comedy game with their peers, playing their way to the next right place (hopefully a funny joke or two!).
Look, we all know that coming up with ideas is hard. As kids we’re taught that ideas are like flashes of light, a bulb that spontaneously turns on and illuminates the answer you’ve been seeking.
In reality, the process of getting there is rocky, messy, confusing and at times leaves us feeling hopeless. That’s often because we’re looking for an answer or creative expression related to work, and work as deadlines, constraints, expectations. We feel like the only place we can play is in our personal lives.
The thing is, ideas, art, businesses, jobs of all kinds, fulfillment, joy, LIFE, all benefit from regular play (what some tragically call “wasting time”). The question is: how might we bring more of that into all aspects of our lives?
This week, Margaret and I forgo conclusions in favor of wandering and exploring the concept of play. We don’t have any answers, just thoughts and ideas. We hope you enjoy 🤸♀️
BONUS EP: The Future of AI and Content + How Content Marketers Need to Evolve
Check your Friday feed for a conversation I had with my friend, David Khim, at Omniscient Digital about the counter-productivity of empathy, the future of content marketing in the age of generative AI, the power of self-motivation, and a whole bunch more. Their podcast, The Long Game, is one of my faves, and I listen to it every week. Definitely check it out.
Gratitude overload
Thank you to our fantastic production partners, Share Your Genius (❤️ Rachel Downey and Katie Mills). If you or your company needs help with media-led growth, reach out and tell them we sent you.
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