Do the weirdest thing that feels right.

From "what to write" to "how to live" | Castles in the Sky #35

While agonizing over what to write last week, I tried to reverse engineer my writing wins. In the process, I discovered that the decision which separated my good writing from my bad writing expanded to my whole life, and was the dividing line between my triumphs and my regrets. 

“Do the weirdest thing that feels right.”

I was shocked to hear myself say it. I had written 10 pages trying to crystallize my attitude toward the wandering, vulnerable, unexpected essays and stories which had resonated with people in the year since I started writing online. I closed my mouth when I saw my own dumbfounded face on the Zoom window. 

“That’s good . . . that’s . . . that’s really good.” My friend stumbled over his words. He was as surprised as I was. He was helping me brainstorm what to write for my 32nd issue of Castles in the Sky, my newsletter. I had originally planned a blithe, meandering roundup of my first year on Substack, but the stakes had gotten a lot higher. 

Three days after my last issue, Substack featured my essay A Pilgrimage for Book People in Substack Reads, the weekly roundup of their favorite things on the platform. I had since been flooded with compliments and congratulations, and my subscribers had grown by sixty percent. Castles in the Sky 32 would be the first email from me a lot of these readers would receive, and so I was torn: should I keep writing about whatever felt right, or should I pivot and narrow down to writing mostly essays about book people? 

Talking it through with my friend, I decided there was more I wanted to write about than bookstores and book people, and I’d rather lose subscribers because of who I am than keep subscribers for who I’m not. But then the question remained, what should I write about? So we reviewed which essays had “worked.” 

A Pilgrimage for Book People was popular, but that was a deeply personal essay nobody else could have written and I spent months with multiple editors on it. Ironically, the essay which was most popular before I was featured in Substack Reads, Requiem for Sean in D Minor, was about something totally different and I wrote it in forty minutes, never expecting anybody to read it. After that was an essay about how cool my Mom is, why supporting small businesses is a moral decision, how an extinct tree reminded me of my deceased uncle, and–even though the likes weren’t as high–I still regularly get messages concerning a short story about an alcoholic who takes a trip to see a magic giraffe. 

My friend asked me how I decided to write those specific essays. And that’s where the mantra welled up from: 

“Do the weirdest thing that feels right.” 

It was so obvious, yet so elusive. Immediately, so much about my writing became clear. What I should focus on became obvious. I felt silly about ideas I had where I was playing dumb status games or “shoulding” myself. I started to draft the notes that would become this essay. 

Later that night, I told my wife about it all before bed. As I was falling asleep, I sat bolt upright. The usefulness of this imperative wasn’t limited to my writing, it was a line through my entire life, separating my triumphs and my regrets. 

I don’t think I’m alone in spending a lot of time wondering what the right thing to do is. Not like, “should I steal candy from this baby?” but like, “How should I balance my career and artistic endeavors? How do I vote? How much doom and gloom should I tolerate in the news to be an informed citizen? How do I model a balance of hope and realism for my child?” 

It’s not that I’m not sure when something is right or wrong–wrong choices are clear. It’s that there seem to be so many options that all feel right. With endless research, discussions, daydreams, and deliberating, sometimes I forget what I actually think is right, or why I think the things I do. 

I was laying in bed after talking to my wife thinking about a decision at work where there were a lot of good things I could do, and from nowhere I asked myself, “of all these good options, which is the weirdest?” And it became abundantly clear. 

I realized that when I think that something is ‘weird,’ it is not really about what I think at all. What I am actually doing is modeling what I think other people will think about it. For example, if I was going to order a lunch delivery, and I thought to myself, “well, I wouldn’t mind a ham sandwich, or a pepperoni pizza, or two dozen raw oysters,” I would probably think to myself, “Oysters? Weird.” But I don’t think oysters are weird, I think that other people will think it’s weird. 

Weirdness is a construct that is a stand-in for other people’s expectations. 

So if I have a bunch of equally viable options, I should pick the weirdest one, because it means that is the one that is truest to me. It means it has had to elbow its way in past what other people think, other people’s expectations, and any insidious fear I have of being judged for doing what I want or what I think is right. In the scenario above, yes other people might find it strange, but I should Doordash two dozen raw oysters. 

And looking back at my life, I can easily find examples where I did something ‘weird’ and it went great, and where I didn’t do what was ‘weird’ and it was terrible. 

For example, when I was 22 I moved to China with no language skills, no job, about $500, and no place to live. It was a weird decision but an amazing experience I wouldn’t trade for anything. But then I was thinking about leaving China after two years or so. My boss basically talked me into staying because he said I might be able to get into an Ivy League MBA Program. I didn’t really care that much, but the idea of that prestige was so seductive (and not weird) that I stayed another year, the last eight months of which were pretty awful. 

My life is one long chain of times where I did something that I thought was weird and it went great, and times when I tried not to be weird and it went awful. Two things I hold in high value are self-knowledge, and overcoming fear. “Do the weirdest thing that feels right” is a way to immediately see where I’m afraid, and to better understand myself. 

I plan to write about this a lot more, but I’m sharing it here because it’s been so useful for me already in just a week. It helped me short-circuit the culture war hamster wheels I found myself on after scrolling social media. It helped me decide which workout and diet to do. It helped me plan activities with friends. And it helped me decide that I should write this essay. 

Because while I do want to write more about book people, the right people will appreciate that this essay is equal parts autobiographical, vulnerable, entertaining, and insightful. And maybe someone will read it, and with an upcoming choice they’ll ask themselves, “what’s the weirdest thing that feels right?” And a world where people are always asking themselves that is one I want to live in.