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

@SargentJamesA are you sure you identified _the_ problem, or are you possibly only treating the symptom of a more fundamental problem?

I have opinions and suspicions. But I want to hear yours.

@poleguy

Trail doesn't fix thinking; it can't. What it fixes is drift. It's solved the problems I've experienced with AI-assisted development: decisions lost in chat, AI filling gaps it shouldn't, and no record of why things were built the way they were. Clear intent, separated roles, and file-boundaries help prevent that. Poor thinking upstream still results in poor outcomes. Trail just makes that clearer faster.

@SargentJamesA this seems like a problem for conventional development too. With a solo developer maybe not so much, but on a team I frequently see drift because intent is not recorded anywhere and one developer doesn't remember, know, or care what the last one intended.

I also notice few developers leave comments or commit messages that answer the why question, and LLM's often delete my comments that encode intenet.