This research project is based upon the assumption that humanity is passing through a period of great transition, or “Great Turning,” in which we have a critical opportunity to pass from a destructive “industrial growth society” to a “life-sustaining society” (Macy and Brown, 1998). I argue that the current scale of social, political, environmental, economic, psychological, and spiritual challenges reflects an underlying “disconnect disorder” (Arabena, 2006), and that these combined external and internal crises present an opportunity for widespread transformative learning and a collective shift. My core hypothesis is that this transition depends on humanity’s ability to engage in a dual process of individual and collective transformation through remembering our connections with ourselves, with one another, with the natural world, and with a sense of purposeful engagement in the world. I investigate this hypothesis through an in-depth, relational study of the Ecology of Leadership program (EOL) at the Regenerative Design Institute (RDI) in Bolinas, California, an organization that aims to “serve as catalyst for a revolution in the way humans relate to the natural world.” The Ecology of Leadership represents a unique model of transformative adult education that incorporates the principles of “inner permaculture” and regenerative design to support participants in cultivating personal and collective transformation. I introduce a “relational” theory and methodological approach, which centralizes Indigenous and ecological principles of relationship, respect, reciprocity, and regeneration. Using interviews (p=20), surveys (p=409), arts-based data (p=12), sharing circles (p=8), and participatory research, I integrate personal and participant narratives together with images, graphics, poems, and practices to bring this case study of the Ecology of Leadership to life. I also advocate for a new model of “regenerative research,” in which the research itself is life-giving and contributes to the healing, transformation, and regeneration of the researcher, the community of research, and the whole system. Based upon my interactions, observations, and interviews in the EOL program and my reflections and supportive research, I conclude by articulating the “Ecology of Transformation,” a holistic model for transformation that incorporates inner and outer change with practices for reconnection to oneself, the natural world, and the village.