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Software engineers care a lot about being smart and knowledgeable. Conversations about how to become a better software engineer often center around learning more facts: programming language syntax, design patterns, details of how particular technologies work, and so on. It’s also undeniable that having a strong working memory is really useful, if only so you can fit more of a codebase in your head. However, there’s a whole other dimension to being a strong software engineer that doesn’t get talked about as much: character. What do I mean by character? I mean the kind of person you are: the quality of your internal self. For want of a better word, your “virtue” or “moral fiber”. In my experience, people with good character are dramatically more effective software engineers. There are approximately one million books about learning software engineering skills and approximately zero books about software engineering character. It’s a bit unfashionable today to talk about character, for some…
How do projects fail at large tech companies? As I’ve said many times, failure means executives aren’t happy with how the project turned out. At healthy companies, that typically means that a sensible engineer wouldn’t be happy either, because the project didn’t work or users hated it. But what actually causes the projects to fail? I’ve seen a lot of projects go wrong - both up close and at a distance - in the last ten years. Here are the main reasons why. Doomed from the start Lots of projects fail because there’s no way they could possibly have succeeded. In American law, some cases get dismissed at “summary judgment”: even if the plaintiff succeeds in proving everything they aim to prove, it still wouldn’t add up to demonstrating enough illegal activity to win their case. At tech companies, some projects are like that: even if the plan goes off without a hitch, the project is still doomed to fail. Some doomed projects begin with over-ambitious plans. For instance, an executive…
What does it mean to get things done? In the abstract, you can complete a mathematical proof or a problem set, but the real world is much fuzzier. Suppose I plant a tree in my backyard. Once the sapling is in the ground, is that done? Not really. There’s always more work to do: clearing the ground around it, watering, keeping pests away, pruning, and so on. Programming large web applications is more like planting a tree than completing a mathematical proof. Once you write a service, you can keep working on it forever if you want to. In large tech companies, this fact is a trap for competent but unagentic engineers. They see an infinite queue of tasks that they’re capable of doing, and they start delivering a stream of marginal improvements to a particular subsystem. From their perspective, it feels like they’re crushing it. After all, they’re putting out work at their top speed: no downtime, no waiting on other teams. But they’re not doing their actual job, which is to deliver the most…
There’s a brand of tech influencer now that’s all about sharing the perfect prompt for any situation. The tweets in question typically read something like “this prompt will make you superhuman”, or “this prompt will be a 20k growth consultant in your pocket”. There’s a kernel of truth here - it’s surprising how much small alterations in a prompt can affect the quality of language model outputs - but overall it’s just a bit silly. Searching for the perfect prompt is just not how you should be engaging with language models. I’ve believed for a while that getting good at AI is not really about “prompt engineering”. Instead, it’s about getting a sense of what language models are good and bad at, of when it’s useful to continue a conversation with a LLM and when you should back out and start a brand-new conversation, of when to use reasoning models and when not to, of when you can broadly trust the model output and when you need to go over it with a fine-tooth comb, and so on. For instance…
I have delivered a lot of successful engineering projects. When I start on a project, I’m now very (perhaps unreasonably) confident that I will ship it successfully. Even so, in every single one of these projects there is a period - perhaps a day, or even a week - where it feels like everything has gone wrong and the project will be a disaster. I call this the valley of engineering despair. A huge part of becoming good at running projects is anticipating and enduring this period. The start of a project always feels good. I have a clear idea of what needs doing, and there’s plenty of time to do it. The very end of a project usually feels good too - by that point all the important pieces are ready, and it’s just a matter of getting the final tweaks and bugfixes in. The hard part is the middle of the project, when all these things are happening at the same time: You’re discovering that some of the things you thought would be easy are actually surprisingly hard New requirements have come…
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Today's links The worst possible antitrust outcome: Hope you like enshittification. Hey look at this: Delights to delectate. Object permanence: Amazon drivers hang phones from trees; DVD Jon v Windows DRM; Chevron's dirty tricks. Upcoming appearances: Where to find me. Recent appearances: Where I've been. Latest books: You keep readin' em, I'll keep writin' 'em. Upcoming books: Like I said, I'll keep writin' 'em. Colophon: All the rest. The worst possible antitrust outcome (permalink) Well, fuck. Last year, Google lost an antitrust case to Biden's DoJ. The DoJ lawyers beat Google like a drum, proving beyond a shadow of a doubt that Google had deliberately sought to create and maintain a monopoly over search, and that they'd used that monopoly to make search materially worse, while locking competitors out of the market. In other words, the company that controls 90% of search attained that control by illegal means, and, having thus illegitimately become the first port of call for the information-seeking world, had deliberately worsened its product to make more money: https://pluralistic.net/2024/04/24/naming-names/#prabhakar-raghavan That Google lost that case was a minor miracle. First, because for 40 years, the richest, most terrible people in the world have been running a literal re-education camp for judges where they get luxe rooms and fancy meals and lectures about how monopolies are good, actually: https://pluralistic.net/2021/08/13/post-bork-era/#manne-down But second, because Judge Amit Mehta decided that the Google case should be shrouded in mystery, suppressing the publication of key exhibits and banning phones, cameras and laptops from the courtroom, with the effect that virtually no one even noticed that the most important antitrust case in tech history, a genuine trial of the century, was underway: https://www.promarket.org/2023/10/27/google-monopolizes-judicial-system-information-with-trial-secrecy/ This is really important. The government doesn't have to win an antitrust trial in order to create competition. As the saying goes, "the process is the punishment." Bill Gates was so personally humiliated by his catastrophic performance at his deposition for the Microsoft antitrust trial that he elected not to force-choke the nascent Google, lest he be put back in the deposition chair: https://pluralistic.net/2020/09/12/whats-a-murder/#miros-tilde-1 a But Judge Mehta turned his courtroom into a Star Chamber, a black hole whence no embarrassing information about Google's wicked deeds could emerge. That meant that the only punishment Google would have to bear from this trial would come after the government won its case, when the judge decided on a punishment (the term of art is "remedy") for Google. Yesterday, he handed down that remedy and it is as bad as it could be. In fact, it is likely the worst possible remedy for this case: https://gizmodo.com/google-wont-have-to-sell-chrome-browser-after-all-but-theres-a-catch-2000652304 Let's start with what's not in this remedy. Google will not be forced to sell off any of its divisions – not Chrome, not Android. Despite the fact that the judge found that Google's vertical integration with the world's dominant mobile operating system and browser were a key factor in its monopolization, Mehta decided to leave the Google octopus with all its limbs intact: https://pluralistic.net/2024/11/19/breaking-up-is-hard-to-do/#shiny-and-chrome Google won't be forced to offer users a "choice screen" when they set up their Android accounts, to give browsers other than Chrome a fair shake: https://pluralistic.net/2024/08/12/defaults-matter/#make-up-your-mind-already Nor will Google be prevented from bribing competitors to stay out of the search market. One of the facts established in the verdict was that Google had been slipping Apple more than $20b/year in exchange for which, Apple forbore from making a competing search engine. This exposed every Safari and iOS user to Google surveillance, while insulating Google from the threat of an Apple competitor. And then there's Google's data. Google is the world's most prolific surveiller, and the company boasts to investors about the advantage that its 24/7 spying confers on it in the search market, because Google knows so much about us and can therefore tailor our results. Even if this is true – a big if – it's nevertheless a fucking nightmare. Google has stolen every fact about our lives, in service to propping up a monopoly that lets it steal our money, too. Any remedy worth the name would have required Google to delete ("disgorge," in law-speak) all that data: https://pluralistic.net/2024/08/07/revealed-preferences/#extinguish-v-improve Some people in the antitrust world didn't see it that way. Out of a misguided kind of privacy nihilism, they called for Google to be forced to share the data it stole from us, so that potential competitors could tune their search tools on the monopolist's population-scale privacy violations. And that is what the court has ordered. As punishment for being convinced of obtaining and maintaining a monopoly, Google will be forced to share sensitive data with lots of other search engines. This will not secure competition for search, but it will certainly democratize human rights violations at scale. Doubtless there will be loopholes in this data-sharing order. Google will have the right to hold back some of its data (that is, our data) if it is deemed "sensitive." This isn't so much a loophole as is a loopchasm. I'll bet you a testicle⹋ that Google will slap a "sensitive" label on any data that might be the least bit useful to its competitors. ⹋not one of mine This means that even if you like data-sharing as a remedy, you won't actually get the benefit you were hoping for. Instead, Google competitors will spend the next decade in court, fighting to get Google to comply with this order. That's the main reason that we force monopolists to break up after they lose antitrust cases. We could put a bunch of conditions on how they operate, but figuring out whether they're adhering to those conditions and punishing them when they don't is expensive, labor-intensive and time consuming. This data-sharing wheeze is easy to do malicious compliance for, and hard to enforce. It is not an "administrable" policy: https://locusmag.com/2022/03/cory-doctorow-vertically-challenged/ This is all downside. If Google complies with the order, it will constitute a privacy breach on a scale never before seen. If they don't comply with the order, it will starve competitors of the one tiny drop of hope that Judge Mehta squeezed out of his pen. It's a catastrophe. An utter, total catastrophe. It has zero redeeming qualities. Hope you like enshittification, folks, because Judge Mehta just handed Google an eternal licence to enshittify the entire fucking internet. It's impossible to overstate how fucking terrible Mehta's reasoning in this decision is. The Economic Liberties project calls it "judicial cowardice" and compared the ruling to "finding someone guilty for bank robbery and then sentencing him to write a thank you note": https://www.economicliberties.us/press-release/doj-states-must-appeal-judge-mehtas-act-of-judicial-cowardice-letting-google-keep-its-monopoly-power/ Matt Stoller says it's typical of today's "lawlessness, incoherence and deference to big business": https://www.thebignewsletter.com/p/a-judge-lets-google-get-away-with David Dayen's scorching analysis in The American Prospect calls it "embarassing": https://prospect.org/justice/2025-09-03-embarrassing-ruling-allows-google-search-monopoly/ Dayen points out the many ways in which Mehta ignored his own findings, ignored the Supreme Court. Mehta wrote: This court, however, need not decide this issue, because there are independent reasons that remedies designed to eliminate the defendant’s monopoly—i.e., structural remedies—are inappropriate in this case. Which, as Dayen points out is literally a federal judge deciding to ignore the law "because reasons." Dayen says that he doesn't see why Google would even bother appealing this ruling: "since it won on almost every point." But the DoJ could appeal. If MAGA's promises about holding Big Tech to account mean anything at all, the DoJ would appeal. I'll bet you a testicle⹋ that the DoJ will not appeal. After all, Trump's DoJ now has a cash register at the reception desk, and if you write a check for a million bucks to some random MAGA influencer, they can make all charges disappear: https://pluralistic.net/2025/09/02/act-locally/#local-hero ⹋again, not one of mine And if you're waiting for Europe to jump in and act where America won't, don't hold your breath. EU Commission sources leaked to Reuters that the EU is going to drop its multi-billion euro fine against Google because they don't want to make Trump angry: https://www.reuters.com/legal/litigation/google-adtech-fine-hold-eu-awaits-lower-us-car-duties-sources-say-2025-09-02/ Sundar Pichai gave $1m to Donald Trump and got a seat on the dais at the inaguration. Trump just paid him back, 40,000 times over. Trump is a sadist, a facist, and a rapist – and he's also a remarkably cheap date. Hey look at this (permalink) Apologies: You Have Reached the End of Your Free-Trial Period of America! https://www.theatlantic.com/newsletters/archive/2025/09/america-free-trial-services/684072/?gift=jQN1t1D1nkO2TQodBiz5KLmz9qdi35_pconlf7F6jjg The Happiest Place on Earth https://ramblingreaders.org/book/442124/s/the-happiest-place-on-earth the brompton-ness of it all https://backofmind.substack.com/p/the-brompton-ness-of-it-all I am a Private Citizen Seeking to Hold My Government Accountable. Dr. Vinay Prasad, a Government Doctor, Killed My YouTube Channel. https://sciencebasedmedicine.org/vinayprasadlovescensorship/ Lawbreaking as a Method of Competition https://papers.ssrn.com/sol3/papers.cfm?abstract_id=5433014 Object permanence (permalink) #20yrsago DVD Jon cracks Windows streaming video DRM https://www.theregister.com/2005/09/02/dvd_jon_mediaplayer/ #15yrsago German “secure” ID cards compromised on national TV, gov’t buries head in sand https://web.archive.org/web/20100826072237/http://www.thelocal.de/sci-tech/20100824-29359.html #15yrsago Applying “ownership” to links, public domain material does more harm than good https://locusmag.com/2010/09/cory-doctorow-proprietary-interest/ #5yrago How to report on vote-by-mail https://pluralistic.net/2020/09/02/free-steven-donziger/#write-the-vote #5yrsago Amazon's weird, terrible Flex https://pluralistic.net/2020/09/02/free-steven-donziger/#chickenized-flex #5yrsago Chevron's dirty tricks against environmental lawyer https://pluralistic.net/2020/09/02/free-steven-donziger/#free-donziger #5yrsago Russia didn't hack Michigan https://pluralistic.net/2020/09/02/free-steven-donziger/#mittenski #5yrsago Amazon drivers hide phones in trees https://pluralistic.net/2020/09/02/free-steven-donziger/#phone-trees Upcoming appearances (permalink) Ithaca: AD White keynote (Cornell), Sep 12 https://deanoffaculty.cornell.edu/events/keynote-cory-doctorow-professor-at-large/ DC: Enshittification at Politics and Prose, Oct 8 https://politics-prose.com/cory-doctorow-10825 NYC: Enshittification with Lina Khan (Brooklyn Public Library), Oct 9 https://www.bklynlibrary.org/calendar/cory-doctorow-discusses-central-library-dweck-20251009-0700pm New Orleans: DeepSouthCon63, Oct 10-12 http://www.contraflowscifi.org/ Chicago: Enshittification with Anand Giridharadas (Chicago Humanities), Oct 15 https://www.oldtownschool.org/concerts/2025/10-15-2025-kara-swisher-and-cory-doctorow-on-enshittification/ San Francisco: Enshittification at Public Works (The Booksmith), Oct 20 https://app.gopassage.com/events/doctorow25 Miami: Enshittification at Books & Books, Nov 5 https://www.eventbrite.com/e/an-evening-with-cory-doctorow-tickets-1504647263469 Recent appearances (permalink) Nerd Harder! (This Week in Tech) https://twit.tv/shows/this-week-in-tech/episodes/1047 Techtonic with Mark Hurst https://www.wfmu.org/playlists/shows/155658 Cory Doctorow DESTROYS Enshittification (QAA Podcast) https://soundcloud.com/qanonanonymous/cory-doctorow-destroys-enshitification-e338 Latest books (permalink) "Picks and Shovels": a sequel to "Red Team Blues," about the heroic era of the PC, Tor Books (US), Head of Zeus (UK), February 2025 (https://us.macmillan.com/books/9781250865908/picksandshovels). "The Bezzle": a sequel to "Red Team Blues," about prison-tech and other grifts, Tor Books (US), Head of Zeus (UK), February 2024 (the-bezzle.org). "The Lost Cause:" a solarpunk novel of hope in the climate emergency, Tor Books (US), Head of Zeus (UK), November 2023 (http://lost-cause.org). "The Internet Con": A nonfiction book about interoperability and Big Tech (Verso) September 2023 (http://seizethemeansofcomputation.org). Signed copies at Book Soup (https://www.booksoup.com/book/9781804291245). "Red Team Blues": "A grabby, compulsive thriller that will leave you knowing more about how the world works than you did before." Tor Books http://redteamblues.com. "Chokepoint Capitalism: How to Beat Big Tech, Tame Big Content, and Get Artists Paid, with Rebecca Giblin", on how to unrig the markets for creative labor, Beacon Press/Scribe 2022 https://chokepointcapitalism.com Upcoming books (permalink) "Canny Valley": A limited edition collection of the collages I create for Pluralistic, self-published, September 2025 "Enshittification: Why Everything Suddenly Got Worse and What to Do About It," Farrar, Straus, Giroux, October 7 2025 https://us.macmillan.com/books/9780374619329/enshittification/ "Unauthorized Bread": a middle-grades graphic novel adapted from my novella about refugees, toasters and DRM, FirstSecond, 2026 "Enshittification, Why Everything Suddenly Got Worse and What to Do About It" (the graphic novel), Firstsecond, 2026 "The Memex Method," Farrar, Straus, Giroux, 2026 "The Reverse-Centaur's Guide to AI," a short book about being a better AI critic, Farrar, Straus and Giroux, 2026 Colophon (permalink) Today's top sources: Currently writing: "The Reverse Centaur's Guide to AI," a short book for Farrar, Straus and Giroux about being an effective AI critic. FIRST DRAFT COMPLETE AND SUBMITTED. A Little Brother short story about DIY insulin PLANNING This work – excluding any serialized fiction – is licensed under a Creative Commons Attribution 4.0 license. That means you can use it any way you like, including commercially, provided that you attribute it to me, Cory Doctorow, and include a link to pluralistic.net. https://creativecommons.org/licenses/by/4.0/ Quotations and images are not included in this license; they are included either under a limitation or exception to copyright, or on the basis of a separate license. Please exercise caution. How to get Pluralistic: Blog (no ads, tracking, or data-collection): Pluralistic.net Newsletter (no ads, tracking, or data-collection): https://pluralistic.net/plura-list Mastodon (no ads, tracking, or data-collection): https://mamot.fr/@pluralistic Medium (no ads, paywalled): https://doctorow.medium.com/ Twitter (mass-scale, unrestricted, third-party surveillance and advertising): https://twitter.com/doctorow Tumblr (mass-scale, unrestricted, third-party surveillance and advertising): https://mostlysignssomeportents.tumblr.com/tagged/pluralistic "When life gives you SARS, you make sarsaparilla" -Joey "Accordion Guy" DeVilla READ CAREFULLY: By reading this, you agree, on behalf of your employer, to release me from all obligations and waivers arising from any and all NON-NEGOTIATED agreements, licenses, terms-of-service, shrinkwrap, clickwrap, browsewrap, confidentiality, non-disclosure, non-compete and acceptable use policies ("BOGUS AGREEMENTS") that I have entered into with your employer, its partners, licensors, agents and assigns, in perpetuity, without prejudice to my ongoing rights and privileges. You further represent that you have the authority to release me from any BOGUS AGREEMENTS on behalf of your employer. ISSN: 3066-764X
From GPT-5 to nano banana: everyone is getting access to powerful AI
