Enshittification; AI common sense; academia’s crisis: Newsletter 22 October 2025

Newsletter 120. Why enshittification is this century’s most important economic trend, getting beyond AI hype and counter-hype, a new imprint for Hollis Heimbouch, plus three people to follow and three books to read.

Is enshittification reversible?

The essayist and novelist Cory Doctorow just published the most significant economic treatise of the Twenty-first Century. It’s called Enshittification: Why Everything Suddenly Got Worse and What to Do About It. Do not let the title put you off. This is a serious work of economic analysis, focused on the impact of technology on business, media, and all of our lives. What we do about these ideas will determine the future we live in. It’s also written in a fascinating and extremely entertaining way. Really: Get yourself a copy and read it. You’ll never think the same way about big tech again.

In 2008, when Charlene Li and I published Groundswell, we foresaw a hopeful future for social media as a positive force that would enable people to draw strength and support from each other and counterbalance the power of corporations and other institutions. Now, in 2025, social media is amplifying the basest and most divisive elements of our psychology, swallowing our energy, depressing our youth, and spreading to pollute every corner of our lives.

What the hell happened? And what can we do about it?

Cory Doctorow’s book provides a clear answer to these questions. He describes an inexorable three-step process by which platforms like Facebook go from delightful new experience to trash-, hate- and spam-saturated wasteland.

• Stage 1. Good to Users. Supported by investors money, a tech company creates a product — a platform — that satisfies a real need. Because the platform is connected, it provides real-time feedback to those running it, who continually improve it to make it better, more useful, and more compelling for users. It grows exponentially to monopoly proportions. The platform starts with open connections to the world (APIs) that enable it to piggyback on other successful elements of users’ experience.
• Stage 2. Good to Business Customers. Having created a compelling environment that’s essential and hard for users to leave, the platform seeks ways to monetize. In the case of Facebook and many other examples in this book, that includes selling targeted ads based on the vast data collected about users, and enabling publishers to drive traffic through the platform. These business customers benefit from the connections. Users put up with them because they’re the cost of using the platform.
• Stage 3. A Giant Pile of Shit. You might think the endgame of a platform is to ramp up the monetization from business customers. But it’s far worse. In the endgame, both the uses and the business customers are trapped as the platform adjusts its algorithm to take more and more of the profits for itself. It ceases to invest meaningfully in platform maintenance like content moderation and instead invests in lobbying to protect its monopoly from regulation. It becomes a crappier and crappier deal for business customers, but remains essential (if your publication isn’t visible on Facebook, how will people find out about it?). All the open APIs get shut down or have toll gates attached. It’s barely usable for users, but they’re trapped in dopamine loops and depend on the platform for connection with other users. And we all say, “This used to be fun, why is it so lame and awful, now?”, even as we go on using it and generating revenue to make the platform owner rich and powerful.

Doctorow cleverly shows that this pattern describes all sorts of platforms. Amazon goes from being a clever way to find and buy almost anything to a wasteland of cheap, poorly designed knockoffs, undermining the world of retail and wringing ever more profit out suppliers and contractors. Twitter goes from high-velocity open sharing platform to porn- and Nazi-filled wasteland.

And as this book clearly explains, now that connected tech is becoming an essential part of everything, the enshittification process is no longer restricted to the online world. It’s the reason your ink-jet printer insists on thousands-of-dollars-per-gallon ink cartridges and stops working when you need it most. It’s why your car surveils your driving habits, narcs to your insurance company, and might end up bricked when it downloads an update.

If you know Cory Doctorow at all, you know his political philosophy is far left of center. But the descriptions here are factual, compelling, and ultimately inescapable. This is no Marxist screed, it’s a sober and well-documented explanation of an inevitable truth. As a close follower of technology trends and ecosystems for the last 30 years, I find these accounts not only fair but revelatory in how much of tech economics they explain. Traditional economics is ill-equipped to explain the tech-enabled economy; this book should take its place as an essential text for the next generation of economic thinkers.

As a reader of Doctorow’s essays, I had already been exposed to a lot of these ideas. What I wanted to know is, Can we do anything about it? That’s the topic of the last 100 pages or so of Enshittification. He assesses four forces that can realistically stop or reverse the march of enshittification: Competition, regulation, interoperability, and tech worker power.

Competition. This happens only if massive platforms are unable to squash rivals. That means antitrust enforcement. Doctorow makes the case that antitrust regulators under presidents from Carter to Trump 1 were reticent to pursue unfair and monopolistic behavior, but Biden’s FTC under Lina Kahn reversed that trend with cases against Google and Amazon. If you’ve pinned your hopes on energized antitrust enforcement, don’t get too excited, because in Trump’s second term it has of course gone back to the same lax enforcement that characterized the previous 20 years. Doctorow is hopeful that we, the voters, can insist on reining in monopolies again. I’m not so sure.

Regulation. This is an ongoing battle. Regulation creates friction that at least in theory slows the enshittification juggernaut. But ask yourself if, for example, the EU’s GDPR privacy regulation has done anything for you but make you click on the cookies button on every web site you visit. Other regulations are in the works. Doctorow calls them a promising step, but still a work in progress. I wonder if big tech lobbying clout will just defang anything political leaders come up with. Doctorow proposes an enforceable rule that “the role of a service is to connect willing senders and willing recipients as efficiently and reliably as possible.” There may be hope, though, in a world where hard-right senator Josh Hawley and his hard-left counterpart Elizabeth Warren agree that tech monopolies need to be restrained.

Interoperability. If a platform controls everything about how you use it and connect with it, enshittification is inevitable. You’re screwed, because the platform doesn’t give a crap about whether it’s got problems, only that you’re stuck with it. This explains why Twitter is full of trolls, but also why the ice cream machines at McDonald’s are almost always broken: connecting to and fixing the problems is technically impossible and sometimes legally prohibited. But there is a workaround. Right to repair laws for vehicles have passed in several states, demanding interoperability. Laws that protect, rather than prohibit, innovators’ efforts to interconnect with tech platforms will inevitably lead to a decline in their power and a trend back toward disenshittification.

Tech workers. Platforms need tech workers. And tech workers generally would prefer to work on improving products, rather than enshittifying them. When the brains of your workforce can at any moment walk across the street to your competition — or start their own tech company — you’re at risk. So at least in theory, tech workers can slow the enshittification process. Noncompete agreements can lock them up, but they’re not enforceable in California. However, demand for tech workers has waned, overseas tech talent is taking plenty of those jobs, and some companies are trying to replace them with AI tools. And under the sway of conservative tech thought leaders like Peter Thiel, more and more tech workers support unbridled platform power.

My take is this: we’re poised on the knife-edge. There is little cause for optimism here, but even so, in Enshittification, Cory Doctorow has laid out not only the dimensions of the problem but the only potential elements of the solution. We still might be able to turn the tide back to a world where tech was a force for improving our lives rather than making them awful and exploitive. That starts with understanding how these trends work, why, and what might stop them. There’s no better way to start on that path than by reading this book.

News for writers and others who think

Anil Dash shares common sense on AI: most tech workers think it’s useful, got some problems, and is vastly overhyped. Sounds about right.

According to Cambridge University Press, academic publishing is at a critical juncture, buffeted by fake AI-generated articles and paywalled journals. Sounds ripe for disruption to me.

Sales of adult nonfiction were down 2% in the first nine months of 2025 (Publishers Weekly, subscriber link). I’m surprised its not worse.

Hollis Heimbouch is launching a personal growth imprint for Harper Collins, Harper Edge, with debut book by Jim Collins (Publisher’s Weekly, subscriber link). Hollis is one of the smartest and most experienced editors in the business; expect good things.

Three people to follow

Adam Larson , founding creative director of Wednesday Magazine, “the bible of dark culture”

Mark Zandi, sharp-eyed economy watcher at Moody’s

Dan Diamond , fiercely independent White House reporter at the Washington Post

Three books to read

Breakneck: China’s Quest to Engineer the Future by Dan Wang (W.W. Norton, 2025). Growth, repression, and China’s engineering mindset.

1929: Inside the Greatest Crash in Wall Street History–and How It Shattered a Nation by Andrew Ross Sorkin (Viking, 2025). How the crash changed America forever — and could it happen again?

The Strategy Trap: Why Companies Fail at Execution and How to Get It Right by Kevin Ertell (Ideapress, 2026). Strategy is hard. But execution is where it usually fails.