Although research has documented the value of art therapy in working with individuals suffering from bereavement, few resources focused on the lasting effects of grief. This arts-based heuristic study compared a series of self-portraits and reflective journal entries, created in response to the death of the researcher’s mother, to identify themes related to the cycle of grief. It investigated the usefulness of personal art making for coping with the lasting effects of grief. A thematic analysis noted major themes that may have implications for adolescents and adults suffering from grief symptoms. Results from this limited study may provide insight into how self-portraiture and reflective journaling in art therapy can be used with this population.