This chapter describes the inner process of a child of eight years who had behavioural and social problems and was under-functioning in school. Drawing class became a place and space of spontaneous expression for this child whose inner world of images shows a borderline situation. It is clear that the libido in the psyche of this child is severely blocked and the outer world has receded in favour of a highly charged inner world. His drawings clearly depict images that illustrate the complexes blocking his process. At one point it is clear that the psyche of this child is in danger of being inundated by inner images incompatible with the ego development of a child of his age. The series of drawings also illustrates the precise turning point in the psyche of this child where the hero archetype influences and activates a new connection to reality. The symbolic meaning of the journeying to the depths and re-emerging is rebirth and freedom from the dominant complex with a return to normal life and development. Alfonso’s process through his spontaneous drawings represents a symbolic journey through the deeper levels of the unconscious and a transcending from one psychological state to another.