Black Swans are unknowable events, by their nature unpredictable, asymmetric and easier to recognize in retrospect: nothing is clear at the outset, there is only an emergent sense of understanding, and traditional diagnose/act/review cycles may trap us into mismatched known responses. The unknowable cannot be mitigated or fully understood through established system, process or formal hierarchy. Instead the unknowable requires diagnosis (emergent under-standing), creation of a coherent narrative (our momentary understanding), sense making (crowd sourcing, interplay between formal and tacit/group knowledge) and reflection (to capture and share). Proceeding through all four steps during all events (including events that only in retrospect are regarded as black swans) requires organizational dyna-mism. Traditional organizations can become exhausted by tackling successive compounding changes. They take hard charging approaches, solve first-order problems, but are tired at the end. Do this constantly, and they become ex-hausted. They are not adapted to this new space. Dynamic organizations have adaptability in their DNA: They don't get breathless; they thrive in change. Typically they have a devolved, distributed strength, based not in systematized, formalized, codified practice, but strong sense making and distributed action. This paper presents a case for building more efficient and agile pathways to cognitive expertise, as described our 2015 I/ITSEC paper, “The Changing Face of Military Learningâ€� (Schatz, Fautua, Reitz, & Stodd, 2015). How do we create learning environments that encourage dynamic responses, sense making, creating diverse teams of different mindsets? How can this be done within the limitations of organizations, like the military, which are by their nature formal hier-archies using formal decision making processes? How do we build learning systems that create inherently curious organizations? To answer these questions, we will present a model for developing adaptable military organizations with the necessary culture and readiness to more successfully confront black swans.