The Gray Area with Sean Illing The Great Enshittening
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Oct 20, 2025 
Cory Doctorow, a journalist and science fiction author known for his work on digital rights, dives deep into the concept of enshittification—the decline of online platforms. He unpacks how this decay happens, starting with Google's 2019 changes and extending to how other industries are affected. Doctorow discusses the reasons users stick with subpar platforms, the implications of monopolies, and the importance of potential reforms in policy and collective action. He poses an intriguing question: can we ever reverse this trend?
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What Enshittification Actually Is
- Enshittification describes platforms that start great, lock users in, then degrade the experience to profit business customers.
- The process repeats as platforms lock business customers and extract more rent, turning services into "a pile of shit."
Monopolies Drive The Decline
- The root cause is changing constraints on firms, especially reduced competition and weak antitrust enforcement.
- Policy choices since the Chicago school era enabled concentration that lets firms degrade products without losing users.
Facebook Bought Instagram To Keep Users
- Doctorow recounts Facebook buying Instagram to retain users who preferred Instagram over Facebook.
- He notes Zuckerberg wrote "better to buy than to compete," showing deliberate consolidation strategy.
