August has been packed with (mostly unplanned) responsibilities (which is its own story), but I’ve somehow still felt like I’m moving through my own quicksand—really oozing through some projects, and wondering why there’s not more breathing room in my day-to-day life. I’ve been thinking about that experience of getting caught up in things, which is sometimes actually unavoidable and other times is…probably pretty avoidable. I wanted to tell you about how that process is playing out in a writing project I told you about in the first Essence of Toast of the year.
This letter focused on an essay I had just started writing about my funny (and wildly subcultural) adolescence. It was to be the new beginning of the book I’ve been working on for the past five-ish years. While this book is very much about the aftermath of those adolescent experiences, until that point I hadn’t actually described them. I hadn’t written about showing up to the 2006 CrimethInc convergence a shy, self-conscious, and intense 16-year old, and hitch-hiking back home freshly addled with my new militant politics. I hadn’t written about the crepuscular joy of riding my bike down University Avenue at dawn or the loneliness of summer vacation or the starry sick regret I felt after trying to wash that loneliness away with too much cheap beer. I didn’t write about how I didn’t yet know what else to do with the mammoth desire for life thrumming through me. But by the beginning of 2022, I’d realized that in order to ask the questions I wanted to ask in this book, I needed to rewind back to this beginning—my own origin story, of sorts.
For months I felt like I was writing different versions of the same first paragraph, like I was opening my mouth but singing in the wrong key. I wrote multiple (unfinished) versions of a story about showing up at the 2006 CrimethInc convergence as a shy but intense 16-year-old: sleeping under a bridge, stirring soup in a giant cauldron, riding my bike through a bleach-white Wal-Mart with a flock of dirty punks. But what was actually interesting about those experiences? How was that story actually setting up the essay? And how to properly emphasize its comic threads without reducing the story to comedy? I felt like I was either being too funny or too serious.
Each awkward start told me that I wasn’t yet at home in the terrain of the essay. While I could conceptualize what it was “about,” I couldn’t quite figure out its tone. Finally, I practically stumbled on the myth of Hermes—who basically scammed his way into the rank of the gods—and figured out the essay’s stakes. While it was definitely about adolescence, it actually about escaping (or attempting to escape) the world one is born into, and the questions I have now about the possibilities and perils in doing so. It’s also about the ways that the real reasons that motivate us to escape aren’t always the one we announce to ourselves and others. (I got a lot of inspiration from Lewis Hyde’s Trickster Makes This World.)
Hermes’ story helped me find the stakes, and I waded further out into the essay. I kept feeling called back into puzzling it out—taking laps into the middle of the pool but turning back around before I reached the end. How to open the essay, now that I knew Hermes was my way in? “Hermes: who was he?” didn’t quite feel right either, like my awkward-opening-syndrome had only transferred its object.
Eventually, I thought of this ridiculously fancy open-air mall close to my last apartment in San Diego—so fancy that housed a Hermés storefront! The mall was almost beautiful—a coi pond, a coffeeshop with ornate cups, winding pedestrian paths—and sometimes I went there to do homework. It was also the closest thing to a gathering place in the non-neighborhood where I lived. I no longer read this fact conspiratorially the way I might have at 16, but that didn’t make it any less grim or lonely to be there, or less odd that this hollowness coexisted with its visual pleasure. I realized that opening with this mall (and my perception of it) could let me introduce the essay’s theme and introduce myself as a character, one with conflicting feelings about the world I’d managed to sneak into as an adult, while also providing a hinge into Hermes’ story—and from there, into an exploration of portals, in-between spaces, and growing up in a world driven by commerce. Most importantly, it allows (or forces) me to claim my role as a narrator in the present—a narrative vantage that’s spacious, rather than one that required weird contortions.
Was it perfectionism that had held me captive in this process, or was there something important that I needed to figure out by re-working the beginning? Now that I am—I hope!—past that holding pattern, I think it was probably a mixture of both. This kind of rumination is one of my writing pitfalls. It’s hard for me to move past something that I haven’t figured out yet, even though I generally think it’s wise to let first drafts be really messy instead of overthinking those early stage. Scratching at the irritation (the itchy discomfort) of not yet knowing how this essay started was a perfectionist tendency. At the same time, through reworking this beginning, I was forcing myself to get really personal—but in my own idiosyncratic way—and to figure out how the essay’s tone was aligned with my intent. I didn’t want to open with a tantalizingly satirical scene from my “depraved” adolescence, but I needed to make peace with it myself in order to find a tone that was honest and vulnerable without being overdramatic. The sharp edge of the beginning made it clear that I was missing the mark.
While there are definitely some things I’d like to do differently moving forward, here are some things that worked well:
I identified the ages/eras in my life I wanted to include in the essay. I knew I wouldn’t write about these ages (or the events they contain) chronologically, but knowing the scope of time I had at my disposal gave me more options for scenes or moments to write about.
I paid attention to the fact that I didn’t feel “at home” in this essay, which was a sign that I hadn’t yet found my voice as a narrator, and also indicated that I as working through bigger questions than “How can I get this scene to sound cool?” I knew that working through the especially sticky beginning would help me work through those questions.
I drafted (and continued to revise) a central document that listed the questions that were of utmost importance for me to explore in this essay. I narrowed this down to one central theme and evaluated the opening (and the essay as a whole) based on how well it matched my intentions. (I talk more about this process in a class I teach called Writing in Unknown Shapes.)
Because I knew that central theme, I was able to recognize when new sources or threads belonged in the essay (like Hermes and shopping malls)!
And here are some changes I’m working to make in my process, to step away from perfectionism and towards a complete draft:
Remind myself that I can always circle back to any unfinished or ambiguous points in the essay when I have a better understanding or fresh ideas—be willing to leave things undone!
Let myself write paragraphs that feel really off-key, especially if I know the content is solid. On that topic, I really enjoyed this podcast interview with Curtis Sittenfeld, in which she compares finding the structure of her novels to assembling dinosaur bones(!), and talks about how that structure is the most important thing for her. (Because I’m more language-driven in my work I think that language and structure are often very connected for me, but I still loved that image!)
Experiment with composing in smaller, vignette-like units that I can complete in a short writing session, in order to incentivize myself to finish messy drafts of entire “units” of this essay.
Exercise more discernment about how many moments/scenes from my life I can or should include in this essay, prioritizing completing a full rough draft rather than plumbing the depths of every possible moment.
While I don’t know if the mall will, when all is said and done, end up being the very beginning of my book, this experience has definitely reminded me of both my tendency to overwork things, and the gift of serendipity that seems to arrive once I’ve found the form, content, and tone whose absence drives that obsessive hunt. (Just a day or so after my “mall revelation,” I chanced upon this interview in the Los Angeles Review of Books podcast with critic Alexandra Lange about shopping malls!)
I feel like it’s so easy to fall into these kinds of obsessive patterns, though, which then have their own frustrated momentum. If you have any similar experiences of your own, please feel free to hit reply and share! I’d love to hear how you wound your way out of it (or how you’re working on doing so now). When you’re working on a project, how do you know if or when you’re “spinning your wheels,” or how does the fear that you are impact your relationship with the project? What strategies do you use for getting out of a holding pattern, or staying calm through what feels like one?
Here’s to wishing us all the gift of serendipity, but also the gift of letting things be unfinished and imperfect! And also a very chill and lovely end of summer! (I’m looking forward to soaking in some sunsets, berry-picking, iced tea and cafe sits, balmy walks, and devouring Andrea Abreu’s novella Dogs of Summer.)
Offerings
Writing in Unknown Shapes — A course for ambitious writers working in ambiguous forms
Practice Space — Drop-in guided writing sessions
Read more Essence of Toast — Archive of past letters
Happiness touchstones
My friend (and wonderfully kind person) Kate Litterer is offering a four-week group coaching program on productivity and goal-setting, called Perceptible Progress. Kate has a critical, holistic, and unique approach to productivity, and I really recommend working with her! I believe enrollment is open through August 31st. You can learn more here!
My friend (and also wonderfully kind person) Kelly McCarthy is doing a fundraiser for the Philly Herb Hub, which provides free herbal support to Black Philadelphians. Learn more here!
I’m loving the overlap of summer and autumn gold here in Olympia (rightful home of the Squaxin Island tribe). I don’t know why but I feel especially tuned into the subtle transitions of the season, though I’m not saying goodbye to summer quite yet!