Training art therapists requires fair grading systems that equitably assess learning styles and developmental levels of academic aptitude, particularly with longer term art assignments. As students progress in their studies, a contemplative education framework offers a self-directed learning environment that strives to share grading responsibilities when evaluating studio projects, which is the focus of this article. The Grading Rubric for Assessing Artwork (GRAA), created by the author, is presented as a self-reporting tool for developing introspective scoring practices while responsibly mitigating overinflated or underinflated self-appraisals. Overall, supporting the advancement of an identity as a practitioner-researcher artist and therapist demands reliable pedagogies that increase awareness of first and third person motivations, goals, and outcomes.