The Heroine’s/Hero’s journey is based on the mythological work of Campbell (2008), The Hero with a Thousand Faces, originally published in 1949. The heroine/hero is the archetype who starts an adventurous journey, following her or his call. Campbell describes myth as essential knowledge of life cycles, transformations, and initiation rites. Out of this idea, 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. The Heroine’s/Hero’s journey is scripted as a holistic change process based on the theory of Staemmler & Bock (1987). Transformative learning theory is concerned about transformative change processes. For this research, the transformative learning theories of Kasl & York (2012) are meaningful since they highlight the intuitive, non-rational, bodily and relational experiences of transformative learning. An essential aspect of transformative learning are disorienting dilemmas (Mezirow, 1991) which is similar to the polarization phase in the Heroine’s/Hero’s journey. This paper draws on a qualitative research based on narrative oriented interviews and co-experienced observations- phenomenologically oriented vignettes. The aim was to explore the dilemmatic experiences of people in relation to transformative learning. How is transformation experienced and particularly the role of disorienting dilemmas in these processes? The polarization phase, the expansive and contractive pole intensify and come into dialogue, was the most significant moment of the journey according to the participants. Especially the emotional, bodily and non-rational experiences of this phase were meaningful.