This article examines the tension between anticipation and resilience as a means to reduce risk. I argue that information drives the processes of order and entropy within a complex, adaptive system, altering both the internal relationships between the parts and the whole and the external relationships between the system and its environment. I examine a set of four theoretical measures of complex, adaptive systems in a case study of the inter-organizational disaster response system that evolved following the Northridge, California Earthquake of 17 January 1994, and assess the extent to which these measures explain the dynamics of the ensuing disaster response system. Striking the balance between anticipation and resilience, order and chaos, requires a process of continual learning. If the ‘secret of safety lies in danger,’ structuring a process for continuous learning is a primary requirement for maintaining creativity and adaptation in practice.