mastodon 4.8.0-nightly.2026-10-06IT leader building privacy-first products with humans and AI. Creator of Trail Framework (CC BY 4.0 + MIT) and TrekCrumbs. I build things with AI and document what breaks. Writing about AI-assisted development, decision-making, and the workflow frameworks I'm developing to prevent drift when execution gets cheap. Conversations drift. Files don't.
I've been thinking about why AI-assisted work breaks down — and it's not the code. It's the decisions. They live in chat, and chat doesn't compound well. I built Trail to fix that.
https://open.substack.com/pub/sargentjamesa/p/the-chat-problem
#TrailFramework #OpenSource #BuildInPublic #ArtifactDriven #AIAssisted #SoftwareDevelopment
Delegation Without Awareness Is Still a Decision
When no one realizes they're deciding, accountability doesn't disappear. It fragments.
When Execution Is Cheap, Ambiguity Is Expensive
Speed only matters if direction is clear. When execution becomes cheap, ambiguity doesn't slow you down; it hides.