Origin story
I was getting some sun in Playa del Carmen when the idea of writing a book called Pants in a Tree arrived fully formed, and I chuckled. That's it. That's how books sometimes begin. With an absurd image that makes you laugh alone in a beach chair.
I'd given myself an insane challenge: write twenty book-length projects in a single year.
“Twenty books is a lot,” I said to myself. “I bet if I can write twenty books in a year, that’d really be something.”
The first step in this challenge was to give myself some notion as to what the titles of these twenty books would be. The fact that "Pants in the Tree" emerged as the third title tells you something about where my head was at.
The weekend sprint
When I got home from Mexico, I sat at my drafting table and doodled out a sketch of the book. I decided on a specific number of chapters, and mapped out what would happen in each one—giving myself obstacles and fodder, little problems for my pantsless genius to encounter. The beauty of this approach was that I knew the shape and many of the moving parts, and I still had plenty of wiggle room to discover why these moving parts were positioned as they were.
What followed was something like a fever dream weekend. I drafted the entire book, following my sketch but letting each sentence surprise me. Take this moment from Chapter 4:
The genius woke in the late-morning heat clinging to the branch of a desert pine.
The only friend he could hope for was the gravity supplied to him by the distance between his body and the earth below.
'Help me down this tree, Gravity.'
I wrote that not knowing where it would go, then subverted my own expectation by having him address gravity as a friend. The whole book emerged this way—writing toward surprise.
The art of not knowing
The process was about "turning a phrase"—writing without knowing where it would land, then following that landing to the next unexpected place. When my genius looks down at the broken sprinkler and says, "There's no need to water the lawn anyway. Go put yourself into a shed somewhere," I, the author, wasn't in on any secret. If there was to be a joke, it wasn't going to be an insider's joke. If the reader was going to wonder what was going on, I wanted to be right there with them in that experience. The sprinkler had become a character, a disappointment, a thing that should excuse itself from the scene. The genius was also sort of talking to himself, wasn't he?
The whole "turning a phrase" approach opened up passages like this one, where observation becomes philosophy:
Perhaps all is as the way I do things. He watched his hands take slow, sloppy steps forward in the cool grass. There may be a wheelbarrowness to things, yes -- that may be part of what everything depends on.
Those statements express a kind of narrative overreach that typify the genius. And maybe myself as well.
The genius crawling on all fours, looking for his pants, suddenly contemplating the essential "wheelbarrowness" of existence emerged from following the logic of the moment.
Enter McIlvoy
After that weekend sprint, I had a draft, but Kevin McIlvoy helped me understand what I actually had. Working with a writing coach helped me find depths I didn't know how to honor.
The tendency in situations like that would be to either push the book toward being simply goofy or attempt to make it profound. Mc helped me go deeper, to thoroughly inhabit the thematic possibilities I'd unconsciously embedded.
He pushed me to flesh out the shock of death that lurked beneath the comedy. The genius had lost his wife, his friend, his grip on conventional reality. Mc encouraged stylistic experimentation and got me to push the work like taffy in different directions. The recurring theme of pants in trees was enough of a spine; everything else could spiral out from there.
The permission of play
A work that doesn't take itself too seriously gives you total permission to go wild. Some of my favorite moments came from this freedom, like when the genius sits contemplating his empty lap:
A lap existed as a part of the perfect balance of things. One's lap, when one stood, was given to someone else who sat down.
This idea was no good because the exchange would only balance if there was an even number of laps.
This is the kind of philosophical investigation the genius was best at—serious thought about absolutely unserious questions, which somehow circles back to being profound. One effect of these ponderings is that they prod at the phenomenon of cognition and compare it in an unfavorable light against the more resonant logic of dreams.
The easiest hard thing
Of all the pieces I wrote that year, "Pants in the Tree" was the easiest and most enjoyable. I don't think "easy" means "simple"—it means I found the right channel for the work to flow through. The absurd premise gave me permission to explore grief, aging, isolation, and existential confusion without the weight of those themes crushing the work.
The book operates on dream logic, where a genius can wake up in a tree wearing only underwear, socks and boots, have a philosophical conversation with gravity, and then insult a broken sprinkler.
Takeaways for writers
The lesson I often make from Pants isn't "write fast" or "be absurd." I use it as an example of how to write a short book based on a sketch. It's a useful example because you can still easily see the signs of the sketch—the arbitrariness of these different elements that each chapter includes.
I gave myself obstacles—pants perpetually ending up in trees—and that constraint energized the creation of the project. I wrote without knowing where phrases would land, and that uncertainty brought discovery. I worked with a coach who pushed me to go deeper into strangeness.
Pants in the Tree began with a poolside laugh and became an exploration of loss and identity. Get your copy here
If you'd like to work with me as your writing coach, reach out to me and let me know what you'd like to work on together.