On this episode of Intentional AI, Chris Bailey and I dig into the idea that sits under everything else: context is king.

The model you pick matters less than the raw material you feed it, so we get practical about what context actually is, why long threads rot and turn the robot dumb, and how thread management fixes it. Chris shares how he loads a session with Wispr Flow and then lets the robot interview him for his blind spots.

I bring a Show and Tell on my Daily Dispatch, the 4 a.m. scheduled task that reads my calendar and tasks and tells me when I’ve overloaded the day. We close with AI news (Claude in Slack, ChatGPT’s scheduled tasks, the burnout paradox) and a few honest experiment check-ins, including the cognitive offloading research that gave us both pause.

If the model is the engine, this episode is about the fuel.