This article outlines an approach to transpersonal enquiry and its application to coaching. It evolves from a personal journey (autoethnography) from the study of fine art principles towards the practice of transpersonal coaching and the actualisation of the theories and principles of transpersonal and coaching psychology respectively. The flow of the journey travels through an appreciation of the creation of art, how to understand art and what this may mean to the individual, the links to some psychological principles and the formation of a methodology which combines the learned elements for the practitioner/participant (coach/coachee) to understand the self in their present condition.