A 500-year-old word for something I’ve been doing since I was 12
There’s an art, architecture, design, and photography bookstore nearby that I adore. It’s a curated collection of interesting things, run by an interesting man. Ross is a creative, who used to work in tech, and now runs a bookstore. Talk about living the dream.
Anyway, we often pop in if we’re walking by, just to chat. And because he loves saying hi to Kona.
During one of those random pop-in conversations, I think we were talking about Italian fashion — or maybe just Italy, or maybe just fashion — and he asked if I was familiar with the concept of sprezzatura.
“Can you spell that?”
Sprezzatura is the art of making something effortful look effortless. Coined in the 1500s, it was originally about how a courtier should dress: thrown together, a little undone, like you couldn’t be bothered, while secretly having agonized over every single thread. The classic move is the bottom button of a suit jacket, left undone on purpose, because doing it up reads as trying too hard.

I recognized it before I went home and researched it to understand it. As Ross was describing sprezzatura, my spiritual bottom button came undone.
I realized I did this constantly in school. I was a good student. Admittedly, a lot of it was because “school” came naturally to me. But there were times I would really study, flashcards, the whole shebang, and then act completely unbothered about the grade, like it had just happened to me. Like the A was something that just happened rather than something I built. If someone asked how much I’d studied, I’d say something like “eh, a little,” which was a lie of proportion if not of fact. I just needed you to think I hadn’t. I needed you to think I wasn’t a try-hard.
I’ve spent a while trying to figure out why. The easy answer is that trying hard and failing is humiliating in a way that not trying and failing isn’t. If you didn’t really try, the failure doesn’t mean anything about you. But I didn’t fail. I got the A. And I still couldn’t let anyone watch me earn it…?
Which brings me to Substack, and the fact that I’m… kinda doing this to you right now.
I write these essays and then I go back and sometimes unpolish them. I polish some things, and deliberately unpolish others. I like it when my voice comes out in my writing, like you can imagine me actually saying these words to you. If a sentence sounds too clean, too composed, like I sat down and crafted it on purpose, sometimes I’ll rough it up. Break it into fragments (not gonna lie, I hate that AI writing loves sentence fragments. That’s how I write! Stop thinking I’m AI!). I’ll throw in a “lol” or a parenthetical that undercuts whatever I just said before it gets too sincere (see previous sentence. And this one). I want it to read like I’m sitting with you and talking to you, not performing for you — but sometimes the talking-to-you voice is itself a performance, workshopped and revised until it sounds unworkshopped. Buttoned all the way up, then one button undone right before you see it. A few well-placed wrinkles so you know I’m a human being living in these clothes.
Social media is just this, run through an amplifier. The #nofilter caption on the photo that took 20 takes. The #iwokeuplikethis selfie that shows perfectly unkempt hair and the golden hour light beaming into a dreamy bedroom. The vulnerable, off-the-cuff caption that got written, deleted, and rewritten five times to find the version of off-the-cuff that read best. We’re all courtiers now, dressing for an audience of strangers, and the whole game is convincing them we didn’t dress for anyone at all.
I wanted to think sprezzatura was the opposite of perfectionism — one is trying so hard it shows, the other is trying so hard it doesn’t. But I don’t think that’s right. I think they’re the same fear wearing different outfits. The perfectionist is scared of what happens if she tries and it’s not good enough. The sprezzatura girl is scared of the exact same thing, she’s just found a way to protect herself from it in advance. She’s nonchalant. If no one knows you tried, no one can tell you the trying wasn’t enough.
I don’t have a fix, or a conclusion. I’m not going to tell you I’ve started leaving my effort visible, announcing how much I’m trying, posting all 20 takes. I am going to tell you this essay feels very meta in that I’m actually not going back to rough it up a bit.
What I do know is that the word followed me home from that bookstore for a reason. It named something I’d been doing since I was 12, something I’m doing in this sentence, probably, if I’m honest, which… see? There. I almost edited that.























