Concepts
Recurring ideas across the essays, organized by topic.
ai
How artificial intelligence and autonomous agents reshape workflows, decision-making, and the nature of human collaboration with machines.
automation
The practice of replacing manual, repetitive processes with systematic ones — and the organizational consequences when those systems become load-bearing.
communication
How information moves through organizations: the signals that carry meaning, the structures that amplify or muffle them, and the cost of getting it wrong.
effectiveness
The discipline of producing durable results — not through heroics, but through clarity, judgment, and systems that compound over time.
engineering
The craft of building and maintaining technical systems, and the organizational dynamics that shape how engineering work gets prioritized, measured, and sustained.
feedback loops
Circular causal structures where outputs feed back as inputs — the mechanisms by which organizations learn, correct, or quietly drift.
finance
The functions that translate organizational activity into numbers: forecasting, revenue recognition, planning cycles, and the judgment calls embedded in each.
operations
The work of maintaining coherence across functions — keeping definitions stable, processes honest, and systems aligned without requiring constant intervention.
org structure
How organizations arrange authority, reporting lines, and decision rights — and the gap between the structure on paper and the one that actually operates.
philosophy
The deeper questions underneath organizational work: what persists, what decays, what we owe the systems we inherit, and how values interact with incentives.
standards
The baselines, definitions, and recurring practices that make progress legible — and the quiet erosion that occurs when they go unmaintained.
system decay
How institutional memory fragments, workarounds harden into process, and organizations slowly forget the reasoning behind their own decisions.
systems thinking
Understanding organizations as interconnected systems where local optimizations create global consequences, and where leverage rarely lives where you expect.
- 2026Somewhere Between Six and Seven16 min
- 2026The Machine Did Exactly What We Asked Of It6 min
- 2025Listening to the Shoulder3 min
- 2025The Clean Line4 min
- 2025Centralize. Embed. Repeat.6 min
- 2025The Perimeter Is Spotless6 min
- 2025Ghost State7 min
- 2025A Vendor Map With Ambitions3 min
- 2025Just Ask Jamie4 min
- 2025Cash Is the Operating System10 min
trust
The slow accumulation of credibility through consistency, transparency, and follow-through — and how quickly it can thin when any of those fail.
