Although the notion of transformative learning points to a desirable destination for educational endeavors, the difficulty in the journey is often neglected. Our intention is to map the experiential micro-processes involved in transformative learning such that the phenomenon is illuminated from a first-person rather than third-person point of view. Employing that point of view, we believe, provides a common frame of reference for both the mentor and the protégé. We employ the notions of liminality, comfort zone, and edge emotions to elucidate the transformative process. The more intimate understandings that result should assist educators to support students who are undergoing such a metamorphosis. In addition, the article will consider some of the challenges encountered by the educator who wishes to support students through this process.