Last year, I was in a community that asked a deceptively simple question: How do you play?
It took me a minute to process the assignment. You see, I don’t play in the traditional sense. You won’t find me on the dance floor or the game field. But I have fun doing what I do, whether it’s following my curiosity, taking a road less traveled, or designing a go-to-market plan.
So I did what I do. I wrote a poem to explore what play means to me. As it turns out, that’s play. Creative play with a touch of attention play, to be exact.
I read my poem aloud to the group. When I finished and was met with silence. Clearly, this wasn’t the answer they were expecting. A few of them, I suspect, walked away thinking I didn’t really know how to play at all.
I’ve thought about that moment a lot since then. So I was eager to read Playful by Cas Holman. (Maybe it would help me become more playful!)
Nothing could be further from the truth. The book didn’t teach me to play differently; it showed me I’m always playing.
I feel like I’ve just been handed a passport for my native country.
Holman — toy designer, former RISD professor, the person behind Rigamajig and play features at the High Line — argues that there isn’t one way to play. And the best play doesn’t have a rule book like sports or games.
Free play is the gold standard: unstructured, self-directed, and internally motivated. It’s open-ended. Has no agenda. Prioritizes process over outcomes. And it happens when you get absorbed in a problem for the fun of it.
Like writing a poem to answer an abstract question.
Holman argues persuasively that most adults have been trained out of it by productivity culture, gender norms, and the mistaken belief that seriousness is the mature alternative to joy.
That framing let me see my own life differently. I’ve always called my business my sandbox — the place where I test ideas, where my teams are encouraged to take big swings and fail boldly. That word turns out to be more than a metaphor; it’s almost literally what Holman is describing. Every day, in work and in life, I treat challenges as puzzles. I turn them over. I play with them. And it’s one of the reasons I’m good at making decisions and finding creative solutions under pressure.
The book validated something I already did, but hadn’t fully claimed: there’s not just one way to play, and playing every day isn’t frivolous. It’s the practice that makes the rest of life workable.
What surprised me most is how joyful Playful is as a reading experience. I expected a manifesto; I got something more like a conversation with a very smart, very curious friend. It’s well-researched without being stiff, full of stories from Holman’s own work as a designer and teacher, and — unsurprisingly — playfully written. (My book is now filled with underlines and comments in the margins.)
If you’re entering adulthood and quietly terrified of what that means, read this. If you’re mired in responsibility and can’t remember the last time you did something for no reason at all, read this. If life is feeling hard, this book is your best resource.
It won’t remove the stressors in your life, but it is an invitation to shift your perspective. Build your own sandbox and start treating your life, your work, and your problems as things you can pick up, turn over, and make something unexpected out of.
Playful is the rare book that can actually change how someone moves through their day.
