Once a company hits a plateau in its market share, the pressure begins to mount.
Investors want more of a return, shareholders want the stock price to go up. Managers pay attention to the metrics they’re held to, and the squeeze begins.
At first, the squeeze focuses on efficiency. Cut obvious costs without diminishing customer delight or the conditions that the employees work under.
That doesn’t pay off forever, particularly in competitive markets.
At this point, there are two options:
The first is to reengage with the market. Innovate. Create opportunities for customers to find more opportunities and value. Use the resources you have to make something better.
The other, which is far more common, is to squeeze people–imagining that they might not notice, and then, with full knowledge that they do, but betting that they don’t have much of a choice.
Diminish the quality of life for employees. Demand more, offer less. Increase stress and forget what the original focus of the organization might have been.
Raise prices but lower quality and portion size and service at the same time.
Fedex decided that answering the phone on the first ring, happily honoring their guarantee and bringing extraordinary service to customers wasn’t as important as increasing their bottom line. Phone trees, unattended email boxes and plenty of fine print all exist to squeeze a few more dollars out of their existing sales.
JP Morgan Chase actively chooses to maximize short-term profit, betting that customers are too entrenched to switch. They’ll invest in coal, amplify credit card debt and outsource whatever they can to increase their margins.
If you use either of these companies, or any of their peers, can you honestly say that they care more and deliver more value than they used to?
Cory Doctorow describes the monopolistic dead ends built into most corporate financing schemes. Enshittification isn’t the decay that comes from neglect. It’s the active squeeze, trading the path of better for the short-term goal of making a few more pennies.
When an organization races to the top, they’re very clear about what they’re doing. They’ll engage their team and the market in a mutual dance toward possibility and improvement.
But when an organization is focused on the squeeze, they know precisely what they’re doing, but will obfuscate and deny instead of admitting it.
I had no idea what “mad magazine autostereogram, cutecore” meant, but it was enough for Midjourney to create this:
Older generations have always been left out of the codewords and trends of the makers of pop culture, but the gatekeepers and lack of shelf space kept pop, popular. There are only 40 songs in the Top 40, only a few hit network TV shows.
Three things have changed:
The long tail means that there’s room for more. Always. As many as 25% of all Spotify songs have only been listened to a few times. The average video on YouTube is seen once a day.
AI generation of art, music, video and writing means that the pace of creation is going to grow exponentially.
Memetic identities, genres and codewords are easier for AI to begin with than complex images. And so, new genres multiply, get exaggerated, evolve and morph into new genres. It’s genetic material, run amok.
The end result is that pop is not popular anymore. It may never be again. The center was a moment in time, but the edges are now everywhere.
When we encounter a thoughtful critic, we need to quickly understand who is speaking to us.
If the work we made was intended for someone just like this, and they don’t like it, we need to do a better job next time. The criticism will help us understand how to improve.
But if the work we made wasn’t for someone with the hopes, needs and expectations of the person we’re hearing from, we can forgive ourselves (and them) by acknowledging who it’s for and why.
This is not the same as not working very hard. In fact, they’re very different.
We’ve been indoctrinated to avoid trying hard (too risky and emotionally fraught) and to resign ourselves to working hard (held up as a virtue).
People who work in productivity-focused jobs where they follow the manual work very hard. If you buy a Subway franchise, you’re buying years of hard work–the more hours you put in, the better your profits. If you work on an assembly line–making chocolate or writing code–the boss pushes you to work harder and harder.
On the other hand, there are projects where the outcomes are less certain and where the manual isn’t as complete. In these sorts of projects, we need to use our judgment and insight. We do things that might not work. There are few prizes for longer work, but plenty of upside for better work.
We’re surrounded by businesses staffed by hard-working people who have been trained to not try very hard. So they stick with the policy and avoid innovation, customer delight and connection.
Ironically, when it’s our turn to be the customer, we often seek out precisely the opposite. Humans are drawn to folks who care enough to try a bit harder.
Left alone, a cup of coffee will gradually cool until it reaches room temperature.
Stable systems regress to the mean. Things level out on their way to average, which maintains the stability of the system.
The same pressures are put on any individual in our culture.
Sooner or later, unless you push back, you’ll end up at room temperature.
(As I write this, the built-in grammar tool has made suggestions to every single sentence, pushing to make it sound less like me and more like normal.)
Here’s a useful writing breakthrough that has made a difference for me…
Set up an account at ElevenLabs. Create a custom voice by uploading some recordings of yourself speaking. It’s not perfect, but it’s eerily close.
Now, when writing an essay, a book or even a report for work, upload the text and have the site convert it to your voice. Download it to your phone and listen to the audiobook you just made as you walk around town or go for a drive.
You’ll probably notice things that didn’t come through when you were trying to edit your own work on the screen.
It’s also a useful hack for anyone writing a screenplay or dialogue. And perhaps it will be helpful for you in converting and then listening to documents that others have written.
Reading is a miracle, but our brains listen differently–especially to our own voice.
You’ll need to fix errors in the code. Adjust errors in measurement. Deal with changing conditions. Perhaps there are systems effects no one could have predicted.
If we begin a project with the high school mindset of getting a good grade (and avoiding the red check), then not only won’t we be eager to find bugs, we’re less likely to invest in projects that might not lead to flawless results.
On the other hand, if we accept that bugs are a useful part of the process, we’re much more likely to end up with a useful result.
“I’m done,” is not nearly as useful as, “this milestone has been reached, let’s go find some bugs.”
The work isn’t to pretend there are no bugs. The work is to eagerly seek out the most important ones.
Those are harsh words. They imply agency, responsibility and failure.
The response might be, “I did everything I was supposed to do.” Or perhaps, “What should I have done? I followed all the instructions.”
Agency and freedom go together. We have more choices than we want to admit. When Ahab decided to become a whaling captain, everything that happened after that was related to his initial choice.
What do we make? The answer is simple: choices.
Owning our choices is a celebration of our future agency. You don’t get yesterday over again, but you do get to make new choices tomorrow.
January 8, 2026
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