Software used to be sharp

The 90s and early 2000s were full of sharp software. Software with rough edges. You’d bump your knee on it if you weren’t paying attention.

Your tamagotchi could die. And it would, regularly, despite all your best efforts.

Your Animal Crossing villagers would get angry at you and refuse to speak to you. They’d stomp around, fuming. They’d move away from your town of their own accord, and there was nothing you could do to stop them.

We’ve moved past this kind of software. Through hard work and technological advancements, we’ve transcended into a world where Animal Crossing villagers always stay if you ask them to.

UIs are, generally, easier to use. Docs are more approachable to beginners. Experiences are smoother and faster. These are good things.

But there’s something about the sharpness of the software in the days of old. There was something that made it feel real.

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On the Neopets message boards, you could use a special kind of markdown called NeoHTML to format your text. It was rife with possibilities to break or go wrong. But it didn’t feel clunky or gritty at the time. It just felt extensible and customizable and cool.

Can you imagine Meta shipping code-based text formatting in 2026? Can you imagine your best friend using it? What about your parents?

Apple famously smoothed out edges. They made computing elegant, aesthetic, and simple. The iPod is still a thing of beauty. The iPhone changed the world. Many others have followed suit. And the world is truly better for it.

But somewhere along the way, we sanded down too many edges. And now software is innocuous, unoffensive, and utterly unoriginal.

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Remember when the App Store opened and the best, most successful apps were completely useless novelty toys: iBeer, a Zippo lighter, and a lightsaber? That feels like ages ago.

We moved from iBeer to commercializing the web with eCommerce, subscriptions, and ads. There was social media, too: first, networks of people sharing their top 8 friends, or filtered photos of their lunches. Then, FaceTuned highlight reels and sponsored product reviews. And now there are agents among us, too.

After all of this, we haven’t figured out what this technology is for yet, nor how to use it. We’re still so early. When it comes to software, we’re still in the iBeer days. We always have been.

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There are a million tamagotchi riffs now. But they never die. They’re just pleasant. It’s not the same. They’re just vapid pets that don’t inconvenience you in any way.

And isn’t that the stuff of community? Isn’t it being inconvenienced, and knowing that your inconvenience is worth it? Isn’t that what it means to have some skin in the game?

Since when is it preferable to have no personal investment in anything? You don’t really believe that “you’re absolutely right” all the time, do you?

We’ve forgotten how to code a tamagotchi that beeps at you incessantly, or one that dies even when you fed it 30 minutes ago.

So, what if we un-smoothed an edge or two? Not all of them; just the right ones.

What if we preserved niche corners of the internet for the right people to find? The ones who want to hand-code a signature for the message boards in an obscure markdown language. The ones who willingly spend their lifeblood building custom extensions, making sure to share them with others. The ones who will appreciate the extra time others took, just to be helpful.

What if we built more of these communities of people with skin in the game?

What if every interface doesn’t need to be a sycophantic agentic chat?

What if we expected more from our users? More depth of thought. More effort. More perseverance.

There’s a danger in making something too appealing. When you try to be agreeable to everyone, you can create something broadly good, but you can almost never make something truly great. Unless you’re Apple. Most of us aren’t Apple.

When we build software, let’s leave some raw edges exposed. Let’s sand enough to avoid splinters. But let’s dignify our users by expecting something of them. And let’s hope that they expect something of us in return.

That’s what community is, after all.