© 2014, © 2014 Taylor & Francis. Art-based learning is a way of engaging the intellectual, affective, visual and kinaesthetic domains modelling creative, lateral thinking and personal meaning-making through metaphor as well as coaching dialogue. It is a form of experiential learning involving learning cycles to entice deep reflection in and on practice and deep, transformative learning. Art-based learning is essential to the studies of Expression and Communication and of Transpersonal Art Therapy (TAT). This journal-type essay explores what happened during an arts-based activity as part of the author’s study in TAT practice. The activity concerned finger-painting ‘the journey of self-realisation’ and the resulting imagery was used to coach dialogue. Describing the process through a series of steps, the author discusses the experiences and insights that emerged during and after the process. Though subjective and not necessarily applicable to all situations, this essay may encourage tertiary educators of studies in Education and Health to employ similar arts-based learning exercises to effectively benefit their own development, that of their students, and effectively the learning community.