Reading
Zero to One
Stablecoins and the Future of Settlement
Dense, but the section on settlement finality is directly useful for payments work.
The Innovator's Dilemma
Reading this alongside some recent fintech case studies to see how well the framework still holds.
Short and often cited, but still worth reading in full rather than by summary.
Thinking in Systems
A clear, patient introduction to systems thinking. The chapter on leverage points is worth rereading on its own.
1997 Letter to Shareholders
Holds up remarkably well. Worth reading once a year.