Posing an inquiry on Mezirow’s transformative learning theory, this study aims to reapproach transformative learning (TL) theory from an enactivist perspective. Grounded in complexity theories, ecological theories, pragmatism, and Buddhist philosophy, enactivism focuses on complex systems where life creates its contexts as a result of biological co-emergence. From an enactivist viewpoint, TL should be illuminated with its focus on what is enacted through reciprocal relationships among organisms and what emerges through communal interaction between organisms and environments. TL should not be limited or located inside an individual, but interpreted and extended toward organisms, environments, and the world. From this viewpoint, this study elaborated Mezirow’s TL theory and enactivism, then reviewed literature that illuminated TL with the concepts grounded on enactivism. The literature review showed that TL emerged and enacted on the intersections of emotional, relational, and ontological domains. Lastly, this study proposed that TL needs to be understood as an ongoing process of transforming its way of being through dynamic interactions, ontological entanglements, and appreciation of wholeness.