Simon Willison on Technical Blogging

"It turns out having an established blog gives you a surprising amount of influence in a field"

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.

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.

Over to Simon…

Why did you start blogging – and why do you continue?

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!

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.

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!

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.

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.

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.

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?

It’s hard to overstate how many opportunities come out of having a well constructed, long term blogging presence.

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.

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.

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.

Writing is thinking. Having a blog helps you practice how to think.

What blog post are you most proud of and why?

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!

I’m going to cheat and pick several:

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.

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 slides and very detailed notes, on the basis that a lot of people won’t sit through a video but they may well skim or even read the blog version.

This particular talk is from DjangoCon 2022 and describes how I use large-scale software engineering practices like issue trackers and documentation and automated tests to improve my productivity on my smaller personal projects as well.

2025: The year in LLMs is my 2025 LLM wrap-up. I did one for 2024 and for 2023 as well. These are a lot of work but I’m really pleased with them. I think I do a solid job of capturing the key trends over the previous twelve months of wild development in the space.

What post was the most difficult to write and how did you tackle it?

The hardest posts to write are the ones where I’m trying to make a convincing argument, especially on a potentially controversial topic.

A good (well, bad) example of that is It’s OK to call it Artificial Intelligence from January 2024. I used a clumsy strawman and ended up having to apologize for how poorly I argued my point.

I’ve grown a pretty thick skin over the years though, especially now that I’m frequently writing about a topic which invites extremely sharp opinions from multiple sides.

Any lessons learned that you want to share with the community?

My number one tip for blogging is to lower your standards! Aim to hit publish while you are still actively unhappy with what you have written, because the only alternative is a huge folder full of drafts and never publishing anything at all.

Nobody will ever know how perfect the thing you intended to write would have been. The flaws you see in your writing are invisible to everyone else.

Your advice for people just getting started with blogging?

Just start. It’s so easy to get caught in the trap of obsessing over the design of your blog, and planning for content that you never actually get around to writing. As long as each entry has a date on it and a permanent URL, it counts as a blog. I think adding an Atom or RSS feed is important too, but you can get started without one - don’t treat that as a blocker.

Don’t worry if nobody reads it. People are unlikely to stumble on your blog organically, but what matters is not the quantity but the quality of your readers. If the only person who reads your blog is a hiring manager that you send a link to, and that gets you an interview, your blog has already paid itself off many times over.

I wrote What to blog about describing types of content that are both low friction and high value: TILs (Today I Learned) and writing about your projects, neither of which have any expectations of shining new insights never seen before on the web. I also really enjoy link blogging, and wrote about that in My approach to running a link blog. Posting to a link blog often takes just 15 minutes and is a great way to bring short-form writing to your blog.

Set up an email list as soon as you realize that your blog is going to be an ongoing thing. Way more people want to subscribe via email than via RSS readers. I didn’t realize this until 20 years into my blogging journey and I’ve been kicking myself for not getting email subscribers sooner than that! I use Substack and literally copy and paste my blog into it, which keeps my cost of sending email at zero.

A few blogs that you particularly enjoy?

Interconnected by Matt Webb presents a delightfully eclectic mix of interests.

Daring Fireball has been one of my key blogging inspirations for 20+ years.

Drew Breunig is a recent addition to my feed reader who always feeds me something new to think about.

The Fly Blog remains my favourite example of a company technical blog, with a very distinct voice and a constant stream of high signal articles.

Anything else you want to add?

Use AI thoughtfully. Look for opportunities where AI helps you produce something better than if you had gone without it.

I don’t like letting LLMs write for me, but I also have 20+ years of writing experience to lean on. I still use them to assist my writing: as a thesaurus, as a proofreader and occasionally to check that the argument I’m making does not have any embarrassing holes.

Sophisticated readers can sniff out LLM-generated text, which inevitably hurts your credibility with them. I value my credibility above all else, so I will avoid anything that is likely to hurt that.

***

Note: Simon has shared insights on practically every aspect of writing and publishing. Read more on his blog.