Technical businesses are often started by people who are not very good at business. Someone builds a technical product that people want and are willing to pay for, and then they scramble to figure out how accountants and payroll and lawyers work. If they manage, things keep growing and they keep learning more and more about the business side.
At some point, things get too big and the business hires "the grownups" — people who have optimised businesses before. They want to take things to the next level, hurtle towards more growth, and unlock shareholder value.
This doesn't always fail, but it can. The cool kids call it "enshittification" now, but that's pejorative and misses some of the different ways in which it can happen. So instead of just complaining about it and explaining yet again why it's bad, I want to look at why it happens, even when smart, well-intentioned people are given the reins.
A restaurant analogy
There's a local restaurant that my friends and I go to regularly and often recommend to others. It's not an amazing restaurant, but the food is well priced, the staff are friendly, and the portions of fries are very generous. If you order a burger and fries, you aren't left eyeing your friend's plate, hoping they aren't going to finish theirs because you secretly want another one.
If you read their Google reviews, you see "generous portions" come up in a few of them.
But what's a generous portion? It's not an easy thing to measure. It's vibe-based. If the restaurant hired a "grownup" to come and manage the place with an eye to increasing revenue, the most obvious thing she could do would be to ask the kitchen to take one fry off every plate. They do a lot of fries orders every day, so taking just one from each plate would create several new portions that they could sell at 100% profit. Maybe that's an extra $50/day or $1,500/month. Easily measurable upside, easy to convince people that there's no downside. No one's counting the fries — even the regular customers won't notice the change, and the new ones certainly won't care.
It works! Drinks all around while management looks at the charts going up and to the right, just like they should. Let's do it again!
You can see where this is going. At some point, the portions of fries are no longer generous, but no one knows when that point arrives. If it happens over a slow enough period, my friends and I don't notice the transition either. But at some point we stop feeling like they're generous, and we decide to try somewhere else. Or someone asks for a recommendation and instead of saying "You should definitely go to BurgerSmurger, they have really generous portions of fries" we say something like "You could try BurgerSmurger, they're pretty good." Maybe we didn't even intend to give a less compelling recommendation, but it causes the friend to stop by somewhere else instead.
Creating measurable value while destroying immeasurable value is the most dangerous tightrope to walk because it looks like you're winning every day until suddenly your reputation is gone and you can't easily undo that.
How it applies to the software industry
Software doesn't come with fries, but there are other ways you see the same thing in action. An open-core project releases a new feature that's only for the paid enterprise version. That's OK — you didn't really need it, but it's a small niggle in the back of your mind. You accept it because you know they need to make money and run a successful business in order to keep developing the free features you like.
Then a feature you've been using gets removed. Or you suddenly need to sign up with a phone number to access it. It's still working well. It's high quality software that fits your needs, but the next time someone asks about the space, your "Oh, definitely use AcmeCorp — we've been using them for years and we love it" becomes "Maybe look at AcmeCorp, we've been using it for years and it works for us." The delight is gone in a way that even you yourself don't notice, but it comes across in how you talk about it to others.
Enshittification comes in flavours
OK, maybe that's a gross metaphor, but unlike most takes I've read on the topic I don't think all enshittification is bad. Of course it's important to find a balance between giving everything away for free to make people happy and becoming the next Oracle. Of course priorities change as businesses grow. Of course metrics are important and making lines go up and to the right is the correct thing to do.
But I think a lot of people could optimise their goals better by keeping in mind that not every outcome can be measured. If something intuitively feels like a tradeoff and looks like a clear win — gating a feature, removing community support resources, adding a popup to upgrade — these can all make your revenue and engagement metrics go up, but maybe you're destroying some value that you can't yet see. It's a difficult tradeoff to make if you can only measure one side of it, but that's exactly why you should be cautious instead of charging ahead faster with every "obvious optimisation".