The Best Leadership Newsletter Ever

The Best Leadership Newsletter Ever

348. The Enshitification of Work

While businesses have over-optimized for profit they've sacrificed humanity. Welcome to the age of enshitification.

Nov 24, 2025
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For the love of all things holy, please stop optimizing everything.

I don’t know about you, but I’m old enough to remember when you could search for something on Amazon and actually get a list of the most popular items.

Now the search results are a cereal box of ads, deals and “sponsored” copycats of the actual thing I’m looking for, which is hidden way down below the fold and who the hell has the forearm strength to scroll that far.

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Facebook? Bitch, please.
It’s more like “Adbook”.

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Oh, and do you remember when flying on a plane felt special? I do. Now it’s been overly-optimized. The idea of a great customer experience has been replaced by a prioritization of profit per seat.

This is the enshitification of America - and the same thing is about to happen to your job.

The Enshitification of America

The term enshitification became popular in 2023 when Cory Doctorow (no relation to E.L.) used it to in his blog.

Here’s what it means - and feel free to think of Facebook while I’m describing this.

Phase 1: Companies are good to their users. They grow because they provide value for the users. And that naturally brings in advertisers.

Phase 2: The companies then focus on bringing more value to the advertisers, which means less focus on the users. Quality, meaning and, basically, humanity are replaced for profit.

Phase 3: Users get discouraged and leave, so the company milks the advertisers for all they can.

Phase 4: Then the company dies.

It’s shitty.
We’ve become a nation of enshitification.

The Enshitification at Work

When it comes to the workplace, enshitification means overly optimizing a company’s productivity in order to make as much money as possible. The byproduct of this is sucking the soul and humanity out of the culture.

Here’s the deal - the world is changing quickly, and it’s speeding up with AI. We all know that.

For business leaders, competition is only going to become more brutal.

The new Darwinian model of company sustainability is best defined as “survival of the fastest to innovate.”

Understandably, leaders are increasing their focus on the metrics of financial success. They are doing everything they can to increase profits and lower costs. And that means decreasing their focus on creating a great employee experience.

Once leaders start talking about “increasing productivity”, it usually means “decreasing humanity.”

This is the slow roll down the slope of enshitification.

The Symptoms of Enshitification at Work

Maybe you still have a good culture at work. I hope you do. But that doesn’t mean the enshitification hasn’t already begun. It just means you haven’t noticed it yet.

Here are some clues that the enshitification machine has started moving at your company:

Always-On-ness: In the US, the line between work and life seems to be drawn in invisible ink. Are you getting 24/7 Slack messages? Do you receive constant email alerts?

Creativity is being sacrificed for connectivity.

Red Alertness: Have you noticed that suddenly almost every task is urgent, but nothing is actually important?

Tooled To Death : Between Monday, Slack, Zoom, Teams and all the rest, the tech stack of connection tools has gotten so large, we have become more disconnected than ever.

Automation Overload : We are in a rush to automate our productivity. Now humans are increasingly doing the mundane robot work while we rely on the robots to do the complex human work.

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Any of those symptoms sound familiar?
I thought so.

The enshitification has begun.

How We Got To The Era Of Enshitification

Productivity and humanity used to work in harmony. That shit is over.

Today’s productivity involves the process of stripping out humanity and replacing it with speed and scale.

The sudden popularity of remote/hybrid work hasn’t helped. Some call it “freedom”. Others call it “flexibility”. But the cost of that freedom and flexibility is isolation.

Leaders have become so accustomed to not having people around, that it’s made it easier to disconnect from the humanity of company culture.

Out of sight, out of Slack, out of mind.

There’s a lot less connection, and a lot more convenience. And now everything suddenly feels disposable, including people.

Especially people.

When Work Stops Working

As AI quickly creeps into the day-to-day dynamics of a company’s operations, leadership has crunched the numbers enough to realize that replacing humans with automation can increase output and decrease drama.

AI doesn’t leave dishes in the sink, and its pets don’t poop on the office floor.

It’s no wonder why 70% of employees feel unseen and disengaged.1
The feeling of purpose has been flushed down the toilet.

It seems like we’ve finally optimized the soul out of work.

How to Reverse the Flow of Enshitification

Fortunately it’s not too late to save humanity - or at least save your company’s culture. We can reverse the flow of the enshitification of work. Here’s how.

Create Connection: The lunch break is dead. It’s important that you CPR that baby back to life. Create more moments of human connectivity.

Respect the Border: Let your colleagues have a break from work. Almost every communication system has a “send later” feature. Use it.

Slow Down: Stop glorifying busy and start rewarding downtime and thinking time. Real creativity happens between the work.

Reward Humanity: Celebrate those times of collaboration and curiosity. It’s not just about output and efficiency.

Start Measuring What Matters: The real things that matter are trust, connectivity, and the feeling of working in harmony with people you enjoy.

In The End

If we all don’t put humanity back into work, work won’t work.
Not for your teams.
Not for your culture.
Not for you.

The enshitification of work isn’t inevitable, but stopping it must be intentional.

Start today.

Rehumanize one decision.
That’s all it takes. One relationship at a time.


If this article resonates with you and you want to learn how to build back your company culture, take this free company culture assessment - or upgrade your subscription and get free coaching and free advice!

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My name is Jeff Matlow, I’m a 3x entrepreneur, author, and leadership coach to high-performing leaders. 

Let's talk.

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