This paper describes a novel approach to teaching introductory-level students how to engage with philosophical texts, developed in the context of a philosophy of art course. We aimed to enhance students’ motivation to read philosophy well by cultivating habits of active reading. To this end we created a structured set of three assignments: (1) instructor created digitally annotated reading assignments, (2) a student digital annotation assignment, and (3) required student participation in a collective GoogleDoc “repository of artworks, examples, ideas, and questions.” Student feedback suggests that this set of teaching tools enhanced their sense of agency in approaching philosophical texts.