- "The Collapse of Complex Societies" by Joseph Tainter (Amazon link: https://www.amazon.com/Collapse-Complex-Societies-Studies-Ar...)
- "Normal Accidents" by Chuck Perrow (Amazon link: https://www.amazon.com/Normal-Accidents-Living-High-Risk-Tec...)
Tainter deals directly with the Roman Empire, but the nutshell is the cost of complexity begins to outweigh its returns, requiring more and more resources just to maintain the status quo, until the entire thing becomes weak and susceptible to failures large and small.
- "Panarchy: Understanding Human and Natural Systems" (Amazon link: https://www.amazon.com/Panarchy-Understanding-Transformation...) is also a fantastic book drawing from ecosystem science and proposes a general model for this. It's pretty well accepted in ecological circles but has been criticised for a lack of empirical data. The general model is the same as Tainter's though.
- "The Logic of Failure" by Dietrich Dorner is also a classic! (https://www.amazon.com/Logic-Failure-Recognizing-Avoiding-Si...)
Well worth reading all of the above.
Fresh book recommendations delivered straight to your inbox every Thursday.