This chapter bridges the thinking and practice of organizational learning, knowledge management and complexity theory by using a case study of a learning system. It describes a learning community as a complex knowledge management system and the impact of dynamic self-assessment as an intervention in order to illuminate its own complexity. A knowledge management learning community of novice human systems interveners utilized the principles of dynamic self-assessment to chart the evolution of the system, using the five characteristics of a learning organization as the self-assessment dimensions. Data was collected through observations and interviews with members of the cohort at the end of year one and the end of year two. Using a case illustration, complex interactive and adaptive processes and emergent possibilities come alive and reveal this system's unique socio-historical trajectory. Self-assessment allowed the community to intentionally tinker with its functioning, and to purposefully create open spaces of possibility.