I Outsourced My Midlife Crisis to an AI (It Rebuilt My Website)

This site used to run on Jekyll. Ruby toolchain, dated look, the kind of local dev setup where “quick fix” meant twenty minutes of gem version archaeology before you even touched a template. It worked. It also embarrassed me a little every time I opened it.

So I did what any developer with thirty years in enterprise systems and zero patience left for yak-shaving does: I handed the whole thing to an agent and said, more or less, “make this not Jekyll.” Astro, Node/npm only, no Ruby in sight. Deployed the same way as before — GitHub Actions, building from master — just with less ceremony to get there.

The part I actually cared about was the design identity, and this is where it got a little indulgent. I’ve spent my career building enterprise systems, including a genuinely-named failover system called “Blackout.” So the site now looks like an ops console: dark navy and brass by default, a status line that says “nominal,” and a counter in the header that ticks up your career like server uptime — seconds and all — computed from the day I started in 1995. It is a completely unnecessary amount of design commitment to a joke about being old. I regret nothing.

Not everything survived contact with actual use. I shipped a “notes” section — a microblog, lighter than the main blog — because it seemed like the kind of thing a personal site should have. Then I sat down to actually write one and realized I couldn’t tell you what it was for that a blog post wasn’t already doing. So it’s gone. Zero notes were harmed, because zero notes were ever written; the whole feature had a lifespan and never once had content. That’s either a clean kill or a confession that I planned before I needed, and I’ll let you pick.

I also went back and pulled my resume out of a hand-typed TypeScript object and into a YAML content file, same pattern as the blog posts, because “my job history” being coupled to “code that ships” felt backwards the moment I looked at it straight.

And yes — I’m aware of the bit where I write a blog post about using Claude Code to rebuild my site, using Claude Code to draft the blog post about it. I thought about writing this one by hand, on principle. Then I remembered I live within my limitations same as anyone, and one of those limitations is a strong preference for spending my evening doing literally anything else. So: mostly its typing, my opinions, my edits, my call on every line that stayed. Ops console theme was mine. The self-awareness about the irony was also, embarrassingly, mine.

Status: nominal.