Writing
Thoughts on building software that lasts, AI that actually helps, and lessons from two decades of production code.
2025
Rebuilding My Personal Brand Decades In
The uncomfortable process of repositioning after decades of building systems instead of reputation.
I'm Not 'Just a Healthcare Person' (And Why That Label Cost Me Millions)
Breaking out of vertical pigeonholing - how domain expertise becomes a trap and what transfers across industries.
Why 'It Just Works' Meant I Was Underpaid for 15 Years
The invisible work paradox - when doing your job well means nobody sees the disasters you prevented.
Measuring AI Output Quality: The Evaluation Harness
How to score AI outputs with rubrics, regression checks, and decision-focused metrics instead of gut feel.
The Five Levels Nobody Told You About: From Junior Dev to CTO
The real hierarchy of technical talent - from junior dev to CTO - and why understanding these levels prevents expensive hiring mistakes.