Crossing the Uncanny Valley

A rope footbridge stretching across a fog-filled mountain valley at sunrise, distant peaks glowing on the far side

Field notes from the workshop. Part one of an ongoing series.

You've seen websites that a machine built. You might not have known it in the moment, but you felt something. Everything on the page was fine. The colors worked and nothing was broken. And still, some quiet voice in the back of your head whispered that no person had really been here. That a template had been filled in. That you'd seen this exact site before, wearing a different logo.

That whisper has a name. Designers and roboticists call it the uncanny valley, and it's one of the strangest features on the whole map of technology.

Here's the idea, told plainly. Picture a long road that climbs toward "looks like a real person made this with care." When a machine's work is obviously a machine's work, we relax about it. A cartoon robot doesn't unsettle anyone. But as the work gets closer to human, something odd happens. The closer it gets, the more the tiny wrongnesses start to glow. A face that's almost right feels worse than a face that's clearly a drawing. So the road dips down into a valley right before the finish, a low, foggy place where things look almost human and feel faintly haunted. Cross all the way to the far side and the feeling lifts. The work simply reads as real, as something a person chose. But that valley in the middle is where most things get stuck.

Websites have their own version of this valley, and we'd spent months down in it.

We set out on a simple-sounding quest. We wanted to build truly great websites for small businesses, the kind of design a plumber or a neighborhood restaurant could never dream of affording from a top studio, and to do it at a price that actually made sense. Early on, our builder made sites that were good. Genuinely good. But they lived in the valley. They had the look of a talented designer who'd run out of inspiration, competent and tidy and just a little soulless.

And they had tells. Every category of business somehow drifted toward the same menu and the same safe arrangement. Worse were the small wrongnesses that are pure uncanny valley: a photo cropped and then centered a hair off, so a person's face sat slightly wrong on the page. The kind of thing you feel a half second before you can see it. We spent night after night hunting these gremlins down and teaching the system not to make them again. For every one we banished, the work crept a little closer to the far ridge, and the fog stayed thick.

Then, a few nights ago, we walked out of the valley without realizing we had.

It was an ordinary night, which is how these things tend to go. Caleb was building out our store-and-checkout features. I was on the other side of the work, deep in the part of our system that decides how a site should look. I'd been at it for twelve hours already. Late in the evening I finished a big stretch of that work and did the thing we always do after we touch how the builder designs: I kicked off a fresh site, almost on autopilot, and turned back to hash out some technical decisions with Caleb.

When the build finished, we opened it. And I stopped.

My first thought was that we'd done something new. This didn't look like our builder on a good day. It looked like a designer had sat with the brand and chased an actual idea all the way through. Caleb, who is wiser than I am about not getting excited, talked me down. The builder had made beautiful sites before, he reminded me. This was probably just the high end of what it could already do. A lucky roll of the dice.

Fair. So we tested it the way we always test, which is by trying to break it.

The most reliable way we've found to break an AI is absurdity. These systems learn from the real world, and they get wobbly when you hand them something the real world would never produce. So over time we'd invented a few deliberately ridiculous businesses to throw at the builder. The flagship of our nonsense fleet is a company called McPoopyPants Potty Polishers. I'll let you sit with that name for a moment.

Nobody has ever started McPoopyPants Potty Polishers. There's no template for it and nowhere safe to hide. We kicked off a build.

It came back wonderful. Not safe, not generic, but a real and specific design with a personality that fit the joke, full of choices a thoughtful human would have made on purpose. So we ran another brand. Then another. One after another after another, each one its own thing, each one looking like intentional work by someone with taste. The sameness was simply gone. The fog had lifted, and somewhere in the climb we'd stepped onto the far ridge without ever hearing the music swell.

Straight from the workshop
McPoopyPants Potty Polishers
The McPoopyPants Potty Polishers website the builder generated: a dark, marble-and-cedarwood luxury layout with an oversized outlined wordmark, a 'Shop the Look' boutique section, and an editorial footer
Booth · Las Vegas
The Booth restaurant website the builder generated: a warm, wood-paneled supper club hero with glowing pendant lamps, the headline 'The best moments of your life probably happened in a booth,' and a 'Reserve a Booth' button
Two builds from that same night. Left: our flagship nonsense brand, McPoopyPants Potty Polishers. Right: a Las Vegas supper club called Booth. Same builder, one kickoff apart — and each one its own thing.

I want to be careful here, because I respect you too much to oversell. We went looking to see whether anyone else is getting results like this, and as far as we can tell, nobody is talking about having crossed this particular valley. I'm not going to plant a flag and crown us the first at anything. I'll only tell you what's true: we haven't seen websites built this way, looking this intentional, anywhere else yet, and we're a little stunned to be the ones writing it down.

And I won't pretend we did it alone. I don't really believe anyone does anything alone. Caleb was instrumental in this as well. Before the two of us, there were the people who built the tools we build on top of, and a long lineage of design thinking we learned from without ever meeting a soul who taught it. Crossing a valley is mostly a story about the bridges other people left behind for you.

So this isn't a victory lap, and it isn't the end of anything. It feels more like reaching the top of one ridge we'd been climbing toward for months, catching our breath, and seeing for the first time how far the mountains actually run. There's a lot of range still ahead. We have notebooks full of it.

But we crossed something real this week. The websites coming out of our workshop stopped looking like a machine made them and started looking like someone cared. For a plumber who could never have afforded that, and for the people behind every small storefront in town, that's the whole point.

More dispatches to come.

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