Simon Willison on Technical Blogging - by Cynthia Dunlop

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Simon Willison on Technical Blogging<br>"It turns out having an established blog gives you a surprising amount of influence in a field"<br>Jan 15, 2026

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New year, new round of tech blogger interviews. Let’s kick it off with Simon Willison: co-creator of Django and creator of Datasette. Over the course of two decades, Simon has built a remarkable body of work at simonwillison.net. His blog ranges from rigorous long-form analyses to pithy link commentaries and lots in between. He’s particularly well-known for offering a pragmatic – and independent – take on AI in software development.<br>In past posts, we’ve shared the mantra “You’re not writing enough” (Bryan Cantrill quoting Pat Helland quoting Jim Gray). Simon, who blogged every day for an entire year, sets a high bar for what’s possible here.<br>Get Write that blog! updates in your inbox

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Over to Simon…<br>Why did you start blogging – and why do you continue?<br>I started my first blog before I knew it was called a “blog” - I was an enthusiastic online gamer back in 1999, and I ran a competitive league for Team Fortress Classic clans. I decided to build a “news site” about the game using NewsPro, a freeware (not Open Source) Perl script. You can still see it in the Internet Archive!<br>I started my personal blog a few years later at university in 2002. I was continuing to learn web development and found a huge amount of value in the small cadre of existing blogs about that topic, so I decided to join in.<br>My previous online activity had been tied to my gamer handle, Skunk. I called my blog “Simon Willison’s Weblog” because I wanted to deliberately start attaching my real name to my writing. This felt quite subversive back in 2002 when most online activity was still pseudonymous!<br>My blogging back when I started was an extension of my all-consuming message forum habit. I realized that forums were centered around specific interests, but often you find someone who is an interesting writer and who you want to hear from about a wider range of topics.<br>It also felt like blogging gave me a direct connection to some of the top experts in the world of web development that I was just getting started in, and the idea that they might link back to me was intoxicating.<br>That was all a long time ago. I took a break from blogging while I was running a startup (and then recovering from that), from around 2010 to 2017. In 2017 I started up again, because I realized that I really missed having a corner of the internet that was all my own.<br>Then the AI thing started to happen towards the end of 2022 and I found myself as one of the few remaining long-form bloggers who was following that space closely. It turns out having an established blog gives you a surprising amount of influence in a field, so I’ve been leaning into it. The effect is the same as it was for web development back in the early 2000s: I get to meet all sorts of interesting people and learn more effectively thanks to those connections, plus writing and thinking with an audience in mind.

What has been the most surprising impact of blogging for you?<br>It’s hard to overstate how many opportunities come out of having a well constructed, long term blogging presence.<br>Most of the jobs I’ve had in my career can be attributed at least partially to my blog. I’ve also been invited to speak at conferences, I’ve had freelancing and consulting opportunities, and most importantly there are a whole lot of people out there with a basic awareness of who I am and what I’m interested in, which can turn into a great conversation any time in the future.<br>I’m a big believer in the idea of making your own luck - setting things up that increase the chances of a lucky scenario landing on you. Having a blog is a wildly effective way of doing that.<br>One other significant benefit that’s worth highlighting: blogging is a fantastic way to get better at writing. It’s a free venue for writing for a potential audience as often as you like. Even if nobody reads it you’re still incentivized to think carefully about your words and how you use them, and any conversations about your work will be certain to help you do better next time.<br>Writing is thinking. Having a blog helps you practice how to think.

What blog post are you most proud of and why?<br>That’s a really hard one - I’ve published 3,251 long-form and 9,607 short-form posts to my site over the years!<br>I’m going to cheat and pick several:<br>Here’s how I use LLMs to help me write code from March 2025 is the most comprehensive piece I’ve written about AI-assisted programming. Most of it still holds up today, though I need to produce an updated version that explores how far into the Claude Code hole I’ve fallen over the past few months.<br>Coping strategies for the serial project hoarder is an example of a format I really like - an annotated presentation. Every time I give a talk at a conference I later write that up on my blog as...