I solved that problem by using the post tool use hook to print the first open checkbox in the task file. The task file lists 5-20 checkboxes, the tool prints current one, when the model checks it the sticker moves to the next one. Like an instruction pointer or a small memory of "what am I doing now".

But this is trivially solved by Plan Mode, or TodoWriter tool. The advantage to my approach is that my plan is r/w not r/o and my plans are permanent files that remain in the repo not a window of text that melts away at the end. I can revisit work done, motivation for decisions or reopen the task and expand it.