Human societies have grown tremendously in scale over the past 10,000 years. However, such a trend is punctuated by frequent reversals, including periods of stagnation and also more dramatic “collapses”. Over the same time period, there were also significant changes in organizational features of human societies, raising questions about the interrelation of these. This talk will start by posing the general question about connecting polity size, “complexity,” and stability. I’ll then show how some of these interconnections can be investigated using the Seshat databank. Finally, I’ll show some of our ongoing efforts to match empirical results with simulations.