Not every repetitive task is worth automating. Some tasks feel tedious but resist automation because they require subtle judgment at every step. Others feel complex but are actually just long sequences of mechanical steps. Knowing the difference saves you from building automation that never delivers, or manually grinding through work a script could handle. I've found that three questions reliably separate the automatable from the not-yet-automatable. They work whether you're evaluating a candidate for AI assistance, a custom script, or a full workflow tool. This framework also applies to choosing what to build versus what to shed, as I explored in Tactical Work Shedding.

I've written before about personalized software as the hidden iceberg of the AI era. Software that was never economical to build, but that people genuinely want. I keep coming back to this idea because I keep building more of it. My latest example is so small it barely qualifies as a project, and that's exactly what makes it worth talking about.

People are building incredible things with AI coding tools. But there's a quieter, equally powerful use case: using Claude Code as an operational partner. DevOps work is half investigation, and AI coding tools are remarkably effective at analysis, script generation, and iterative diagnostics alongside a human who handles execution and judgment.