experiment

reorienting my life around "play"

Andy Warhol, After the Party, 1979

This month, I hosted a murder mystery dinner party for twelve friends. I’d never participated in one before, but I had the vague idea that ChatGPT could be employed to come up with the murder scenario and characters. I intentionally designed the game to ensure that anyone could be a suspect. Every character had a motive, and the killer was assigned at random. Clues, planted around the apartment, were just vague enough to allow for doubt about who they referred to. The best mysteries are the ones that keep us guessing because it’s fun to have theories and to prove our theories wrong.

This year, I’m trying to orient my life around a mindset of play rather than work. Play and work often refer to separate spheres of activity, but I want to challenge that notion. The best work comes from play—from an attitude of curiosity and a practice of experimentation.

Last week, I attended David Nebinski’s podcast recording with Anne-Laure LeCunff where she talked about the benefits of conducting tiny experiments over discrete periods of time to learn, iterate, and overcome challenges. She has a great quote in her upcoming book, which I’m paraphrasing here, that success is the journey of finding what makes us feel alive. What I love about this is that it positions success as an active, continuous process of discovery rather than a finite, fixed outcome at the end of a journey. Success is the journey.

Outcomes in play are uncertain, and not knowing what will happen is part of the fun. That doesn’t mean you can’t have desired outcomes, but those aren’t the reason we play. When kids play tag in the park, they’re not doing it so they can make someone “it.” They’re doing it to have a good time. Pure play is generative and boundless, whereas work demands efficiency, measured in output per unit of energy or time.

A friend asked me if I viewed writing as work, and without hesitation, I answered no. For me, writing shares greater affinity with play. Experimentation is inherent in the practice. Writing involves cycles and cycles of trying something new and learning from it. The word “essay,” popularized by Montaigne, comes from the French essai, meaning “trial” or “attempt.” The meandering process of discovering how I—or my characters—think and feel and why is what makes writing so fun.

After winning his first Oscar at the age of twenty-seven, Matt Damon thought to himself, “Imagine chasing that, and not getting it, and getting it finally in your 80s or your 90s with all of life behind you and realizing what an unbelievable waste of your… It can’t fill you up. If that’s a hole that you have, that won’t fill it.”

I’ve had a similar experience chasing something illusory that I thought would fulfill me and talked about it recently on David’s podcast. In 2015, when I first started taking writing seriously, I decided I would write a novel. Very few people who start a novel ever complete one. The challenge was exciting. I woke up at 5:30 or 6 every morning to put words on the page, and a year or so later, I had a finished product that I was very proud of. I shared my manuscript with my mom and eagerly awaited some sign from her that it was the best thing she’s ever read and that I should immediately send it off to agents. Unfortunately, no such sign manifested, and I knew, deep down, that it wasn’t going to sell. This is extremely normal for a first book, but my disappointment was shattering because I’d worked so hard on it for so long. I was plagued by self-doubt: what if I could never write anything good enough? What if I spent my life chasing something out of reach?

I had to remind myself that what I loved about writing wasn’t the prospect of finishing a book or getting published, it was the creative journey itself—full of surprising revelations about your characters, about the kind of story you want to tell, the truth of what you’re trying to say. That’s what sustains me. If I were only doing it for the external stamp of approval at the end, I’d be pretty miserable because it’s a long and arduous journey to get there, and validation is never guaranteed. Landing an agent or a book deal may be nice, but it’s not the point of writing. The point is doing something you really love, which is a tremendous privilege. I once had a boss who, rare in the corporate world, had an MFA in creative writing. He candidly admitted that he gave up on trying to become a published author when he realized it was the idea of being a writer that appealed to him more than the craft of writing itself.

When someone asks me, “How do you find the time to write?” I think what they’re really asking is “How do you motivate yourself?” For a person who loves to write, finding time is not the problem. It’s a bit like asking, “How do you find time to eat a delicious meal?” It’s something you can’t not do.

I used to think that in order to be successful, you had to work extremely hard and earn good grades and ace all your exams and get into a top college and land a well-paying job and get promoted. I used to think that in order to be a true artist you had to suffer for your craft. I no longer believe either to be true. No external measure of success can nourish you, and nothing that nourishes you requires brute-forcing—or, for that matter, pain and suffering. That’s not to say that writing isn’t hard. You can love doing hard things. Sometimes, doing hard things makes you feel most alive. To find out, keep experimenting.