The condition of chronic pain, like other chronic illness, is a phenomena that begs further investigation because of its significant physical and psychological impacts. Additionally, it is an affliction that is difficult to treat, understand and overcome. Traditionally, diagnosis and treatment of this condition has depended on retrospective recall of symptoms, which are often subjected to bias. Current research in medical art therapy has shown promising potential in the treatment of both the psychological, physiological and sociological impacts of chronic pain. However, there is limited arts-based research that steps outside of a medical model. In this research I have used my own experience to deepen the understanding of chronic pain by addressing the following question: How might a daily art practice describe the lived experience of a training art therapist experiencing chronic pain? This was explored using a heuristic, arts-informed methodology. Data was collected through a daily art exercise that responded to the prompt, “Describe your pain today” as well as reflective journaling. The discussion of these images utilizes Jungian theory in order to gain insight into the more intangible meanings produced by the imagery.