Assessment has become a dirty word in arts education, because art is notoriously difficult to assess. Assessment, which is often disliked or even disavowed by arts educators, due to its history of incompatibility with the idiosyncratic nature of arts learning, should ideally be utilized as a means of measuring student progress and help teachers understand how to help students succeed. While assessment can also be used to evaluate programs and teachers and to compare student successes relative to those of other students, I will be focusing on measuring individual student progress for my thesis and building a curriculum to support that. To measure student progress, I have utilized three tools: (1) a modified proficiency-based model for beginning students, (2) co-creation of curricula and assessment for intermediate students, and (3) a goals- based curriculum and assessment model for advanced students. This thesis study chronicles the journey of one art teacher and her high school students towards a more authentic means of utilizing assessment in a contemporary and engaging curriculum.