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Simon Willison's issue-driven development

3 min read

For the past couple of years, I’ve been a big fan of Simon Willison, an open source software developer who helped create Django, and has more recently been interested in AI and large large models. I really admire Simon as someone who is passionate about his work and gets so much done.

Back in 2022 he gave a talk called Coping strategies for the serial project hoarder, which covered how he manages to make progress on so many little projects. One strategy he mentioned is ‘issue-driven development’, where he documents his ideas as GitHub issues, and then talks to himself in comments while he’s working on them. That way, if he drops a project for six months, he can come back and pick up where he left off. It’s a great way to document your work as you go, and clarify your thinking.

I really want to try to get into the habit of working this way. I have a lot of ideas that I start working on and then give up on, maybe because of motivation or running out of time.

Another reason I like this strategy is it helps you learn in public and makes your work easier to share. I’m keen to share my side projects with other developers and get feedback, and also to include these projects in a portfolio.

Over the last couple of days, I’ve been trying to work in this way on my astro-sqlite-tts-feed project. You can read a bit more about this project in my blog post here. I’ve added the following features to the app:

I’m trying not to create too many issues at once, because it becomes overwhelming. It’s like standing at the bottom of a mountain. Instead, I want to keep the issue count low and keep putting one foot in front of the other. As I implement more features, I’m discovering more surface area of the project, and making it better and better.

It’s difficult building up a habit of working in this way. Because I have a few different interests and only limited time to work on side projects, I am always rushing when I work on them. But if I can be a bit more disciplined, I will be able to accomplish more in less time.

Originally published on by Larry Hudson