2025-11-11-checkpointing-conversations-with-claude

When I’m deep in a long Claude session, I use what I call a checkpoint strategy. It’s basically a conversational anchor.

Let’s say Claude throws out a list of ideas or questions. Before diving into one of them, I’ll drop a quick line like:

Use this as Checkpoint A for our conversation — when we come back, track the decisions made.

That way, I can explore one branch in depth, make a few choices, then jump back to the checkpoint and pick a different path — without losing the thread of what’s already been decided.

It’s like branching in Git, but for chat. Each checkpoint keeps the flow organized while I experiment with different directions.