I am right now building a proactive coach on top of my AI work capture app. Concept is very simple: It takes a screenshot every few minutes and analyzes what you're working on. From there it identifies task blocks, and checks if it should start a chat based on your intentions (eg to tell you to move out of your rabbit hole, take a break, help with a task, ...)

https://donethat.ai Passively processing screenshots is obviously pretty sensitive, it has an option to bring your own (local or remote) LLM, otherwise I process with gemini and never store any data.

It's in beta right now so if you want to try it you have to enable "proactive chat" in settings.

I also made a list of similar tools out there: https://donethat.ai/compare