Much of what was once taken for granted about gender roles has shifted, leaving a lack of desirable or achievable roles for men. This text argues that the male psyche has been wounded by the new pressures of social uncertainty and needs to be healed. It explores the concept of masculinity using the work of Ken Wilber as a central guide and Jungian Alchemy as a framework within which to discuss the process of change. The way this change happens is personal to each man and involves aspects of the body, emotions, rational understanding and soul. However, because the change required is so major, what is needed is a continuous process that sees the man through the ups and downs, contradictions and paradoxes along the way. The therapeutic relationship is ideally suited to this task. The efficacy of therapy cannot be taken for granted and the author explores how different sorts of therapeutic intervention can hinder as well as help the processes of change.