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Edition No. 2 MAY 28, 2026 · 37.77° N · 122.42° W Subscribe by email →
An observational journal · est. MMXXVI

Midnight Thinker

Software. Leadership. The ideas that won’t leave me alone.

Tonight
Waxing Gibbous
This week’s transmission
⟡ This week’s transmission
R.A. 4h 27m  /  Dec. −70° 33′

Welcome to the Midnight Thinker Newsletter

The blog now has a newsletter. Here is what to expect.
Date
Read the essay

§ ii

The Log

recent entries, most-recent first
  1. 02

    The Judgment Gap

    Why software design still matters when AI is writing your code

    R.A. 17h 42m
    Dec. +0° 56′

§ iii

On the Desk

books currently shaping the writing
  • A Philosophy of Software Design
    John Ousterhout
    READING NOW
  • Notes on Being a Man
    Scott Galloway
    READING NOW
  • The Art of Leadership
    Michael Lopp
    JUST FINISHED
§ iv

The Author

about the thinker

Rob Cataneo is a software engineer and engineering team lead with fifteen years of practice, based in the San Francisco Bay Area. He spends most of his working life inside the messy, high‑stakes decisions that come with building distributed systems at scale — architecture tradeoffs, technical vision, and the human side of leading engineering teams.

Midnight Thinker is his notebook made public — a place to work through ideas in software engineering, leadership, and the books that won’t leave him alone. No particular schedule, no particular audience. Just thinking out loud, done properly.


§ v

Constellation

topics, sized by frequency

⟡ Dispatch

A nudge when a new essay lands.

Once or twice a month, at most. No drip, no "thought you might find this interesting," no product noise. Just the heads‑up.