How can academicians who desire a sustainable future successfully participate in transdisciplinary projects? Transcending our hidden thought patterns is required. Paradoxically, the disciplinary specialization that enabled the industrial era and its metaphors now function to undermine our ability to recognize and participate in the transformational learning that is needed. In this paper, we offer a post-industrial era metaphor for transdisciplinarity—that of complex dynamic system—that has helped us to work through the unexpected experiences encountered in the process of transformative learning. These insights are based on an ongoing transdisciplinary research collaboration (2008–present) using action research methods; we focus on the faculty experience. Accepting the metaphors of complex systems, we describe the systemic conditions that seem to repeatedly reproduce the emergence of transformative learning for participants, as well as what one might expect to experience in the process. These experiences include: conflict, existential crisis, transformation and renewed vitality within the necessary context of a safe and caring community. Without the adoption of complexity metaphors, these elements would have been overlooked or interpreted as a hindrance to the work. These insights are intended to serve as socially robust knowledge to support the effective participation of faculty members in sustainability projects of a transdisciplinary nature.