TL;DR: I have started this blog countless times in ten years. Each attempt came with a smarter diagnosis of why the last one failed, and each diagnosis was right. None of them worked. Understanding a problem is not the same as solving it, which is embarrassing, because spotting that in other people's work, and helping them past it, is most of what I do for a living.

Here's to my 255th go at starting a blog.

The archive is not kind. WordPress in 2016, a few technical posts, then nothing. Jekyll around 2018, of which almost nothing survives. Hugo from 2021, where the record survives in detail, but only because that's where I started writing about blogging instead of blogging.

Hello World! Again! in 2021: I struck out "57th" and wrote "63rd go", then blamed the days lost to servers, hosting and the About Me page. Again! Again! in 2022: if you do great work and never communicate it, how is anyone meant to know? Early 2023 worked, four posts by mid-February, including a properly technical one with terminal recordings I'd over-engineered for the joy of it. Then it stopped.

March 2024 is where it gets uncomfortable. I wrote the most thorough one yet: audience defined, prime-time hours booked, templates built, a branding course attended, a book read. It ends, "I'm hoping this is my last 'Hello World!' post on this blog."

I never published it. It's still in the repo with draft: true at the top.

2025 named the imposter syndrome and chose good enough over perfect. Then I took that post about choosing good enough over perfect, migrated to Eleventy, and spent a year building a theming framework. A plugin, a separate repo for the theme, four linters, a PurgeCSS safelist with a proper merge model, a devcontainer, a deploy pipeline into S3. The live site served the default starter template that entire time.

At work I ship. There's a date, a team, and someone who needs the thing, and the constraint does the work. It isn't discipline. A deadline is carrying the weight for me, which is much easier and looks identical from outside. Remove the constraint and what's left is what I enjoy, which is taking things apart and making them better. The framework was a pleasure. The post was homework.

Every one of those old posts diagnosed this correctly. Perfectionism, prioritisation, imposter syndrome, process over outcome. All accurate. However, the insight has never once been the fix.

So this time, no resolution and no metric. Just the constraint I never had before: something published, on a schedule, whether or not it's ready. Only took a decade to realise. If you're stuck on something you understand perfectly well, that might be your problem too. You don't need a better diagnosis. You need a deadline and someone expecting the thing.

Here goes nothing: "Hello World!"