An AI state of the union: We’ve passed the inflection point, dark factories are coming, and automation timelines | Simon Willison
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What is the November 2025 inflection point that made AI coding agents reliably write code?
A lot of people woke up in January and February and started realizing, oh wow, I can churn out 10,000 lines of code in a day. It used to be you'd ask ChatGPT for some code and it would spit out some code, then you have to run it and test it. The coding agents, they take that step for you. And an open question for me is: how many other knowledge work fields are actually prone to these agent loops? Now that we have this power, people almost underestimate what they can do with it. Today, probably 95%. code that I produce, I didn't type it myself. I write so much of my code on my phone, it's wild. I can get good work done walking the dog along the beach. My New Year's resolution, every previous year I've always told myself this year I'm gonna focus more, I'm gonna take on less things.
This year my ambition was take on more stuff and be more ambitious.
Such an interesting contradiction. AI is supposed to make us more productive. It feels like the people that are most AI pillar working harder than they've ever worked.
Using coding agents well is taking every inch of my twenty-five years of experience as a software engineer. I can fire up four agents in parallel and have them work on four different problems. By eleven AM, I am wiped out.
You have this prediction that we're gonna have a massive disaster at some point. You call it the challenger disaster of AI.
Lots of people knew that those little O-rings were unreliable, but every single time you get away with launching a space shuttle without the O-rings failing, you institutionally feel more confident in what you're doing. We've been using these systems in increasingly unsafe ways, this is gonna catch up with us. My prediction is that we're gonna see a challenge of disaster.
Today, my guest is Simon Willison. Simon, in my opinion, is one of the most important and useful voices right now on how AI is changing the way that we build software and how professional work is changing broadly. What I love about Simon is that he doesn't just pontificate in the clouds. He's been what you'd call a 10x engineer for over 20 years. He co-created Django, the web framework that powers Instagram, Pinterest, Spotify, and thousands of Other platforms, he coined the term prompt injection, popularized the ideas of AI slop and agentic engineering, and amongst his hundred-plus open source projects, he created Dataset, a data analysis tool that has become a staple of investigative journalism.
What makes Simon rare is that very few engineers have made the leap from the old way of building to the new way as fully and visibly as he has. And as he's leaned into This new way of building, he's been sharing everything he's learning in real time through his incredible blog SimonWilson.net. Simon does not do a lot of podcasts, and this conversation opened my mind up in a bunch of new ways. I am so excited for you to get to learn from Simon. Don't forget to check out Lenny's Product Pass.com for an incredible set of deals available exclusively to Lenny's newsletter subscribers. With that, I bring you Simon Wilson. Simon, thank you so much for being here and welcome to the podcast. Hey, Lenny, it's really great to be here.
I am so excited to have you here. I've been such a fan of yours from afar for so long. I've learned so much from your blog. And even though every guest I have on this podcast is my favorite guest, you're my favorite kind of guest because you're on the ground, building with the latest tools, using it for real. You're very good at articulating what you expect. experience. So we're gonna get a lot of ROI out of this, out of your brain from from from this time that we have together. What I want to start with is essentially uh an AI State of the Union. You've written about this November inflection.
Yes.
So what I'm thinking is we start, just kind of give us like a brief history lesson of just like what happened in November and where are we today? What's possible now?
Well, let's let's talk about all of 2025 very briefly. Um, 2025 was the year that especially Anthropic and OpenEI realized that code is the application.
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Chapters
8 chapters
1
What is the November 2025 inflection point that made AI coding agents reliably write code?
0:00–8:23
2
How are developers using AI agents to build software without writing or reviewing code (the “dark‑factory” pattern)?
8:23–24:38
3
Why are mid‑career engineers feeling the most pressure and how can they avoid burnout?
24:38–42:15
4
How does cheap, AI‑generated code change prototyping and the overall software development process?
42:15–50:30
5
Which AI coding models does Simon prefer and why does he switch between them?
50:30–1:03:26
6
What is the “pelican riding a bicycle” benchmark and what does it reveal about model quality?
1:03:26–1:13:30
7
How does Simon use the “hoarding” and “red/green TDD” agentic engineering patterns to boost productivity?
1:13:30–1:23:33
8
Why is prompt injection called the “lethal trifecta” and how could it lead to an AI‑Challenger disaster?
1:23:33–1:39:48
Speakers
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