This extended abstract presents the Heroine’s/Hero’s journey based on the mythological work of Campbell (2008), The Hero with a Thousand Faces, originally published in 1949 as a space for possible transformative learning experiences. Rebillot (2011) created an experiential approach in the form of a one-week workshop, utilizing methods from theatre, gestalt therapy, bodywork,dance and indigenous rituals. For this research, the transformative learning theories of Kasl & York (2012) and Dirkx (1998) are meaningful since they highlight the intuitive, non-rational, bodily and relational experiences of transformative learning and transformation as a process of individuation. This paper/dissertation (work in progress) draws on a qualitative research of the Heroine’s/Hero’s journey workshop in 2018 and 2017 based on narrative oriented interviews, co-experienced observations-phenomenologically oriented vignettes and my own experience. The aim of this paper is to explore the experiences of people in relation to transformative learning. How is transformation experienced and particularly the role of disorienting dilemmas (Mezirow, 1991) and community in these processes? The power of the community, especially present during the morning circles of active listening, gave the participants a feeling of connectedness where people felt listened to, accepted and valued. Moreover, the experiences of acted out dilemmas, the tension of one’s desire to flourish (heroine/hero) and the part, which holds back (opponent), were intense for the participants and a way to understand one’s situation in a new light.