We are glad to welcome Cory Doctorow—journalist, activist with the Electronic Frontier Foundation, and author of more than 30 books— to CloudFest 2025 as one of our star speakers as we explore the theme of The Human Edge. From contributing to one of the very first widely-read blogs to standing at the front lines of online civil rights battles, Doctorow has always used his voice in service of the internet’s end users. Indeed, it’s difficult for many of us to imagine the online world without him.
CloudFest is coming up soon—but not soon enough! Let’s sneak in a quick pre-CloudFest conversation with Cory Doctorow.
When I think of the work you’ve done over the years, your activism comes to mind first—in fact, your writing introduced me to the Electronic Frontier Foundation (EFF), which defends civil liberties online. Can you tell us a bit about how this decades-long relationship began?
I had helped start a dotcom software company in the 1990s that did peer-to-peer search and file discovery. We had a great team of programmers, including a bunch of hackers from the Cult of the Dead Cow (the same group that Beto O’Rourke later admitted to being a part of!). When Napster got sued, our investors freaked out about being invested in another (very different) P2P company, and our hacker employees put us in touch with EFF.
I hit it off great with them. Later on, when EFF lost its lease in San Francisco, I moved them into part of our company’s office (there were only 6 EFFers then!). Then, when Microsoft offered to buy my company, our scumbag investors did a cram-down round to steal the founders’ equity and cash out big. This was just after the dotbomb crash and there wasn’t anyone else we could go to for bridge finance while we finished the deal.
The investors told me I was lucky, that I would get a great job at Microsoft out of this deal, even if I didn’t make any money from the sale. So I quit the company and went to work for EFF instead. The deal fell through, the investors got nothing, and 23 years later, I’m still at EFF.
You’ve written a lot of material for kids and young adults. What is your system for synthesizing the often-complicated ideas in sci-fi and cyberpunk for those too young to drive? (I may or may not steal some of your pointers for my own newsletter-writing.)
Kids are inexperienced, but they’re not stupid. Kids can often reason well, but they have very little context to reason with. That’s why you get child prodigy mathematicians and chess players, but not child prodigy historians. Math and chess are systems that you can do a lot with if you know some simple precepts and apply some first-rate reasoning. History, on the other hand, requires an awful lot of reading and context to understand. No matter how good you are at reasoning, you can’t understand history until you’ve read a couple hundred books.
All that is to say that I assume kids are good at reasoning, but lack the facts to reason with. Breaking down complex systems is all about talking to someone who is intelligent but inexperienced, and giving them the knowledge they need to understand the concepts.
Most of our audience would have been exposed to your writing since their early days on the web, but you used to have a day-job! You were a sysadmin, if I remember correctly. Do you still follow developments in the data center? If you had to go back to your old job, what would be the hardest adjustment? What would be the easiest?
I barely follow the industry these days, though I have immense respect for the people who do that work. I don’t know what the biggest challenge would be (maybe the HVAC stuff?) but I know that I would LOVE to have had modern devops tooling—staging servers and rolling improvements, all the stuff that would have saved me from so many high-stress, late-night panics when an update broke everything.
“Enshittification” is far catchier than “platform decay”: the term you coined was the American Dialect Society’s 2023 Word of the Year in 2024 and the Macquarie Dictionary’s 2024 Word of the Year. We’ll leave the juice of this topic for your keynote, but can you tell us a bit about how it felt to see a single word you wrote blow up like that? How has that affected your subsequent writing?
The first time I used “enshittification” was in a throwaway bad-tempered rant about the decay of Tripadvisor into utter uselessness, which drew a small chorus of appreciative chuckles about the word.
The word rattled around my mind for five months before attaching itself to my detailed theory of platform decay. But it was that detailed critique, coupled with a minor license to swear, that gave “enshittification” a life of its own. How do I know that the theory was as important as the swearing? Because the small wave of amusement that followed my first use of “enshittification” petered out in less than a day. It was only when I added the theory that the word took hold.
Likewise: how do I know that the theory needed to be blended with swearing to break out of the esoteric realm of tech policy debates (which the public had roundly ignored for more than two decades)? Well, because I spent two decades writing about this stuff without making anything like the dents that appeared once I added an Anglo-Saxon monosyllable to that critique.
Adding “enshittification” to the critique got me more column inches, a longer hearing, a more vibrant debate, than anything else I’d tried. First, Wired availed itself of the Creative Commons license on my second long-form article on the subject and reprinted it as a 4,200-word feature. I’ve been writing for Wired for more than thirty years and this is by far the longest thing I’ve published with them—a big, roomy, discursive piece that was run verbatim, with every one of my cherished darlings unmurdered.
That gave the word—and the whole critique, with all its spiky corners—a global airing, leading to more pickup and discussion.
[Note: Is the Enshittocene part of the larger Anthropocene Era, or has the decay been great enough to consider it its own stage in the planet’s history? That is beyond the scope of this humble article. —Jordan]
The CloudFest community loves to support Groundbreaker Talents, which provides full-time residential scholarships in Software Engineering to students from financially constrained communities in Uganda—and you may even run into some of them at Europa-Park. What advice would you give them about the internet that they wouldn’t learn in class?
Nothing about the internet is foreordained. Every aspect of its functionality, governance, profit centers, and infrastructure was the result of policy choices made in recent history by people who are mostly still alive and just as error-prone as you. The internet isn’t fully baked. It is still pliant. We could have a very different internet. It’s up to us to make it.
CloudFest is calling you
March 17-20, 2025
