Hey 👋,

One thing has been bothering me about AI-assisted workflow tools for a while:

They can help you think clearly in the moment, but they still make you rebuild context the next day.

You have a great planning and development session.

You refine the story.

You update the plan.

You capture design decisions.

Then you come back tomorrow and think:

Which story was I in again?

That’s the problem I just worked on in the Hypothesis Driven Development skill for imdone.

In SCRUM-267, I focused on making the Hypothesis Driven Development skill easier to resume from one day to the next without forcing you to re-find the story or reassemble the state from memory.

Here’s what changed:

- the Hypothesis Driven Development skill now remembers the active story locally

- if you invoke it without a story key, it can reopen the right story automatically

- if the saved story is missing or stale, it asks instead of guessing

- push reminders are now session-aware, so they check during real work and only reset after a successful push

The bigger point is this:

Good workflow tooling should reduce restart friction, not just help while you’re already in motion.

If you lose 10-15 minutes every morning figuring out where you left off, your process is leaking context.

I’m trying to make the Hypothesis Driven Development skill feel more like working in a well-kept repo:

the story, plan, and reasoning stay close enough to the work that you can just pick it back up.

If that sounds familiar, reply and tell me where your workflow tends to drop context.

I’m collecting patterns as I keep tightening this up.

If you want the walkthrough, the video is here:

https://www.youtube.com/watch?v=GE48aDZwfPQ

And the public cheat sheet is here:

https://gist.github.com/piascikj/2ade2c43d0e6bd476c72ac530f126c52

imdone-cli:

https://www.npmjs.com/package/imdone-cli

— Jesse