Drawing on the work of educational anti-consumerists such as David F. Noble (2002) as well as design theory (Cross, 2006; Dorst, 2011; Farrell & Hooker, 2013) and adaptive leadership (Heifetz, Grashow, & Linsky, 2009) we frame the complex interactions involving teaching and learning along a spectrum bracketed by training on one side and education on the other. Training is a process which generates objective knowledge in order to make a person functional within someone else’s system or industry (Noble, 2002, 2013). In other words there is no direct connection to the self or personal development. In contrast, education, at its best, is total integration of one’s self with the knowledge they absorb and eventually synthesize for their own self-learning (Noble, 2002). When choosing between training and education we, as a nation, have often chosen the former in the name of workforce development and economic progress, but at what cost? Unfortunately, the traditional teaching strategies employed throughout modern educational history do not offer a method or model with which to conceptualize, much less begin to solve such wicked problems. Only by understanding the conceptual underpinnings that support contemporary pedagogy and andragogy might we begin to create educational spaces that help us solve such complex challenges.