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October 17, 2025

It's Clippy's world now

There's no avoiding the AI assistants anymore. Except for this one weird trick!

Don’t show me this tip again, Clippy

When Microsoft first introduced its Office assistant, "Clippy," it was ridiculed by many. The cutesy animated paperclip came across as goofy, but the real problem was how annoying Clippy was: He popped up unexpectedly way too often, interrupting your work to offer inane recommendations you would invariably reject. Sometimes you had barely started to write when he jumped in, like an overenthusiastic waiter swooping in to check on your food the instant you take your first bite.

"It looks like you're writing a letter. Would you like me to help?"

No, Clippy -- fuck off. I'll let you know when I need your help, which is probably never.

We mocked Clippy as mercilessly as we did the hypercompetitive yuppies who walked around with wireless "Bluedouche" headsets in their ears, lights blinking, like someone in the early stages of assimilation.

Twenty-five years later and everyone has a Bluetooth headset in their ear -- or both ears, most likely a pair of glossy white Airpods, which don't blink and, thanks to Apple, look more Eames than Borg -- and we can barely open an email, a document, or a search engine without some overeager AI interrupting us with its recommendations. "I'm tired of Google mansplaining to me," one of my friends said recently. Thankfully, the cutesy animated paperclip is no more, but its spirit lingers on in the relentless faux-solicitousness of these irrepressible digital assistants.

(And it turns out you can still get Clippy for your desktop -- only now he's powered by your choice of LLM. I guess that's an improvement?)

Maybe because we're so exhausted by all the cascading catastrophes going on in the world, we can barely muster the energy to complain about this mental pollution, let alone give it the vigorous mocking it deserves. Maybe we're just less in the mood to joke about annoyances than we were in the late 90s and early aughts. Or maybe the tech companies have finally won, giving us what they think we need whether we want it or not. And we take it, because we have no good alternatives.

Or do we? I am writing these words using a Uni-ball Signo and a cheap composition book from Bazic Products, enjoying the cool calm of a library classroom that's quiet enough right now for me to hear the scribbling of my pen against the paper. I've been enjoying the way the blank gel ink unfurls across the page as fast as I can scrawl, and the thin paper takes on a textured feel after I've covered it in words.

And best of all, I'm enjoying the way that my mind makes its own suggestions for what to write next. When I can sit still like this for an hour, I start to be able to hear that voice again, the one that only I can hear. My own internal writing assistant.

photo of a pen lying on top of a page of handwriting
A mercifully AI-free zone

Field Notes

Photos and poems: My friend Janne-Pekke Manninen is just wrapping up a three-month photography residency. I collaborated with him a little, sharing a few guided meditations and poems over the course of the summer. His photos (and some of my poems!) are currently on display at SomoS Gallery in Berlin.

YC hustle: I sometimes work out of the Capital One Cafe in San Francisco (the Tweney Media "retail storefront." When I was there last week, YC founder Nathaniel Ventura set up his own storefront. I admire the hustle!

Haiku for world peace: A diagram from a presentation by Kyoko Uchimura at the Haiku North America conference in San Francisco last month.

New platform: I’m going back to WordPress for my website and using a new email platform, Buttondown, for my newsletter. This won’t make any difference to you except that my emails will be coming from a different server, and they may look a little different than they did before.

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