Simon Willison on Technical Blogging
Publishing imperfect work beats endless revision—lowering your standards is the key to consistent technical blogging that builds career opportunities and professional influence.
Key Ideas
Lower Your Standards to Ship Consistently
Willison's core advice contradicts perfectionist instincts: publish while "still actively unhappy" with your draft. Perpetual revision cycles kill more blogs than poor writing ever will. The flaws that feel glaring to you as the author remain invisible to most readers.
Blogging Creates Asymmetric Career Opportunities
Most of Willison's jobs throughout his career came partially from his blog presence. Beyond employment, an established blog generates speaking invitations, consulting work, and access to interesting people. A single hiring manager finding your work justifies years of writing.
Writing Improves Thinking—Even Without Readers
The discipline of writing for an audience sharpens clarity and critical thinking. The act of explaining concepts publicly forces you to understand them deeply. Blogging serves as valuable practice for written communication regardless of traffic.
Actionable Takeaways
- Remove barriers to entry — Skip the perfect design. A dated post with a permanent URL is a functional blog.
- Start with low-friction formats — TILs (Today I Learned posts), project documentation, and link blogs take roughly 15 minutes each.
- Set up email subscriptions early — More people prefer email over RSS. Willison learned this 20 years into blogging.
- Focus on reader quality over quantity — One relevant reader matters more than thousands of casual visitors.
Notable Quotes
"Having an established blog gives you a surprising amount of influence in a field." — Simon Willison
AI and Writing
Willison uses AI as a tool—thesaurus, proofreader, argument checker—but opposes AI-generated content. Sophisticated readers detect AI text, and credibility matters more than speed. The hardest posts involve controversial arguments, where poor reasoning requires public apology and correction.
Willison's Proudest Posts
- "Here's how I use LLMs to help me write code" (March 2025) — Comprehensive guide to AI-assisted programming
- "Coping strategies for the serial project hoarder" (November 2022) — Annotated conference talk format
- "2025: The year in LLMs" (December 2025) — Annual industry trend summary
Recommended Blogs
- Interconnected by Matt Webb
- Daring Fireball
- Drew Breunig's writing
- The Fly Blog (company technical blog example)