Shape Up
Shape Up changed how I think about project planning. The idea of shaping work into appetites — fixed time, variable scope — is so much more honest than estimating story points. You decide how much time something is worth, then design a solution that fits.
The concept of the “hill chart” for tracking progress is simple but effective. No percentage complete nonsense, just: are we still figuring things out, or are we executing? I use this mental model constantly now, even outside of software.