Against a backdrop of disruptive change, it is tempting to try to categorize and spot patterns early: we have seen a recasting of politics, the upset of established systems, the emergence of new media, challenges to traditional models of learning and an evolution in the nature of knowledge itself. The relentless march of technology masks part of the true nature of this change; while technology is a very visible manifestation of change, it is the underlying sociology, the cohesion of communities, and the evolving forms of power behind them, which really count. In this social age, we are seeing a fundamental evolution in types of power that will disrupt much of the previous power dynamics. This paper builds on previous work that centered on how to re-contextualize scripts and frames to educate organizations to better deal with Black Swans (Stodd, Reitz, Schatz, & Fautua, 2016). Black Swans are disruptive events, unpredictable and disruptive of formal systems. If the nature of Black Swan events is known, then the ecosystem within which they occur is of key interest; as the ecosystem changes, so too does the nature of disruption, the speed with which it occurs, the groups that cause it, and the inability of formal systems to predict or cope with the results. This paper will contextualize these disruptions in terms of types of power, formal and social systems, and the impacts of these effects on learning and leadership today. We propose a learning concept that focuses on increasing strength through highly engaged, high trust, and reputation led, social communities. Additionally, we will provide case studies of military and non-military organizations that have applied similar concepts: they maintain a dynamic tension between formal and social systems which allows them to learn fast, evolve rapidly, and become highly resilient to future black swans.