
Welcome to my new readers; I’m happy to have you here. But I do want to warn you: if you assume, based on my last post, that I write about bots and scams a lot, you’re going to be disappointed.
Mostly I write “personal essays” (with a significant sideline in exploring cool stuff like acequias and track driving and egg cars, and a deep background project exploring the unintended consequences of how we embrace technology.)
It’s ironic that I write personal essays, because sometimes they gross me out. Too often they’re self-indulgent, overly emotional, narcissistic. But when they work, they provide you with a front row seat to watch another flawed human trying to figure out the world … and maybe figure it out yourself as a result.
“When they work” … well, what’s that mean? For me, a personal essay works when it fulfills the terms of this simple and implicit contract: I’m writing about me, but our shared goal is that you learn about and reflect on you. There’s a kind of reciprocity at the heart of the personal essay.
On the writer’s side—my side—I strive to be really honest: I’ve got to present myself as a flawed person, a work in progress, pushing beyond the superficial to gain understanding. This is what I’m trying to get at in the title of my Substack, Out Over My Skis. I think that to some extent we’re all “out over our skis,” trying to make sense of the world and all the weird people in it.
But how honest do I have to be? How deeply into my psyche do I need to take you? It’s one thing to share with you my problem with assholism—as I did in “I’m Confused”—but if I’m honest, that assholism is just a manifestation of an even deeper egotism that ... well, I’m not sure I want to explore.
I got to thinking about this when I read an essay by Amy Yuki Vickers titled “#022 Living on a Spectrum” (linked below). What was most striking to me was the power she brought to the essay by being so incredibly honest and forthcoming about the unique way she saw the world.
The thought of being this forthcoming scares the shit out of me! As I read, I tried to imagine walking down this path ... that is, I got into the neighborhood of “thinks I’m right all the time” and “blunt” and “sling opinions first, ask questions later” ... and I thought, “Holy crap, this is scary!”
Being this forthcoming takes real courage. She was able to pull this off without being narcissistic or maudlin or excessively self-absorbed. She just said: this is the way the world looks from my view, and she didn’t ask for sympathy or concession, just understanding.
The other thing Amy helped me see is that we’re all operating from a different “playbook.” She helped me see that the people I interact with may be operating with a completely different set of “user instructions” than mine. Different goals, different mental models for what makes an interaction successful, different ways of understanding words, and different ways of processing the input of their senses.
Amy says she spends a lot of time imagining “what life is like in other people’s heads”—and I think that’s what we’re doing when we read personal essays. I know that I look for writers who help me see the world in a different way. When I occupy the space that they create for me, I’m able to understand myself and the world more deeply and with more empathy.
It’s essays like Amy’s that make me appreciate Substack, a place where I can encounter other people’s minds and voices, and in listening to them, develop a more empathetic approach to understanding the world. That’s the whole game for me: understanding myself, getting “better” at reacting to the world and to all the people in it who think so differently than I do, coming to terms with my successes and failures and the passage of time ...
Amy’s essay also fulfilled the terms at the heart of the personal essay: by telling me about herself, she helped me understand myself.
Here’s Amy’s essay. I hope you enjoy it.
Thanks for reading.
Love the idea of “out over my skis.”
Thank you again for your very kind and generous post. I'm really happy you enjoyed mine.