Gunderson's and Holling's adaptive cycle metaphor provides a qualitative description of the development of a dynamically evolving complex system. According to the metaphor, a complex system alternately passes through phases of stability and predictability and phases of reorganization and stochasticity. So far, there have been no attempts to quantify the underlying notions in a way which is independent of the concrete realization of the system. We propose a method which can be applied in a generic way to estimate a system's position within the adaptive cycle as well as to identify drivers of change. We demonstrate applicability and flexibility of our method by three different case studies: Analyzing data obtained from a simulation of a model of interaction of abstract genotypes, we show that our approach is able to capture the nature of these interactions. We then study European economies as systems of economic state variables to illustrate the ability of system comparison. Finally, we identify drivers of change in a plant ecosystem in the prairie-forest. We hereby confirm the conceptual dynamics of the adaptive cycle and thus underline its usability in understanding system dynamics.