In this paper it is argued that work on transformative learning has been predicated on assumptions about agency on the part of both teacher and student and suggests an idealised learning environment. While recognising the significance of transformational learning the paper explores what it describes as the shadow side of transformational work, utilising feedback from students in a postgraduate course. The paper begins with a brief overview of transformational education. The changing context of transformational learning is then outlined. The paper considers issues of power, resistance and pain in transformational experiences, before suggesting one possible response to these issues.