As we attempt to “manage in the unmanageable”, referring to Flood (1999), our challenge is to address the systemic and complexity related issues inherent to any system of interest we may wish to examine. For those not versed in systems jargon, reference to a ‘system of interest’ can be described as whatever aspect of reality one chooses to focus on in a systemic manner satisfying the definition of a ‘system’ based on the work of Bertalanffy (1968), compared to what one considers as the environment. By understanding the set of relationships that exist in any system of interest, particularly in human social systems, and the self-organizing factors at play, new insights and theories can be generated to provide more useful approaches to leading and managing within a systemic world. These insights have significant value in addressing issues of sustainability and understanding of how people actually live and work together and how we organize and lead in today’s world of complexity and change. This allows us to manage in the unmanageable.