Leaving breadcrumbs for future me

June 17, 2026

I work on a lot of projects, and most of them go quiet for a while before I come back to them. The hard part was never the work. It was returning to a project weeks later with no idea where I left off, what I'd already tried, or what I was about to do next. I'd lose the first hour just reloading my own head.

So I had Claude help me come up with a breadcrumb system. Every project gets a little file — a breadcrumb. When I stop working, I have Claude write down where things stand: what's working, what's half-finished, the next thing I meant to do, and any weird gotcha I'd otherwise forget (the kind that costs an hour to rediscover). That's it. It isn't documentation, not exactly. It's a note to future me, who I've learned not to trust with remembering anything.

The point is that I don't have to hold the project in my head between sessions. I can let it go completely, because the breadcrumb is holding it for me. When I come back, I read one file and I'm oriented in a couple of minutes instead of an hour.

There's a bonus I didn't expect: it makes working with AI great. I updated my CLAUDE.md files with knowledge of the breadcrumb system and it's caught on instantly. Now it asks me if it should update breadcrumbs when it seems like I'm wrapping up or at a stopping point.

It pairs well with PARA, which keeps my notes organized. PARA is the filing cabinet. Breadcrumbs are the sticky note on the door that says "you were right in the middle of this."

How to set up your own breadcrumbs

You don't need special tooling for this — just a folder and an AI assistant. At the end of a session, paste something like this:

Write me a breadcrumb for this project so future-me can pick it back up cold.
Keep it short and skimmable. Cover:
- where things stand right now (what's working)
- what's half-finished
- the very next thing I meant to do
- gotchas I'd waste time rediscovering (commands, paths, dead ends I ruled out)
- the handful of files that actually matter

Skip anything I could get from the code or git history.
Save it as .breadcrumbs/<project-name>.md

If your assistant has a config file (mine's a CLAUDE.md), you can make it automatic. I added a line like this:

At the end of a work session, offer to write or update a breadcrumb at
.breadcrumbs/<project>.md — where things stand, what's next, and any gotchas.

Now it just asks when I'm wrapping up, and I never have to remember to leave the note.

If you stop and start projects often like I do, give it a try. Future you will be grateful.