The Careful Observer

Notes on craft, code, and quiet persistence

On the Merits of Slow Software

January 28, 2026 · 6 min read

There is a particular satisfaction in software that does not rush. It does not auto-update at inconvenient moments. It does not suggest you upgrade to a plan you did not ask about. It loads, it works, it waits.

I have been thinking about this after spending a week with a text editor written in 1991. The experience was not nostalgic—it was clarifying. The editor did exactly what I asked, nothing more, and the absence of surprise was itself a feature.

We have confused capability with quality. A tool that does forty things poorly is not superior to one that does three things well. The Unix philosophy understood this. Somewhere along the way, we forgot.

Extended Analysis (Members Only)

The economics of slow software are counterintuitive. Projects like SQLite, TeX, and Plan 9 demonstrate that long-term maintenance costs drop dramatically when the initial design is allowed to mature without market pressure.

My rough calculations suggest the total cost of ownership for "boring" software is 3-5x lower over a decade. The detailed spreadsheet and methodology are in the members repository.

R

R. Halloway

Writes about software craft, epistemology, and the odd intersection of the two. Currently building tools nobody asked for.

r.halloway@example.com · Portland, OR

Three Books That Changed How I Debug

January 15, 2026 · 4 min read

Debugging is not a technical skill. Or rather, it is not only a technical skill. It is an epistemological practice—a structured way of asking "what do I actually know, and how do I know it?"

These three books reframed my approach entirely:

  1. How Doctors Think by Jerome Groopman
  2. The Art and Craft of Problem Solving by Paul Zeitz
  3. Seeing Like a State by James C. Scott

The connection between these may not be obvious. Let me explain.

Detailed Reading Notes (Members Only)

For each book, I've prepared chapter-by-chapter notes mapping concepts to debugging scenarios I've encountered professionally. The Groopman book alone gave me a framework for "diagnostic timeouts" that I now use in every incident response.

I've also included a 12-page PDF of my personal debugging checklist, refined over 8 years of production systems work.