Two artist-educators analyzed their creative process informed by John Dewey’s concepts regarding the act of expression. The essay interweaves a description of their performance piece with a discussion of conceptual processes, including intermediality and collaboration as crucial in art making, learning, and pedagogical efficacy. Both the creation of the piece and the written analysis were guided by concepts Dewey identified as compression, impulsion, and expression. The authors argue that experience and expression exemplify creative learning and are transferable to knowledge construction in all areas of inquiry. Throughout an aesthetic learning process, deep reflection plays an essential role with interpretation and application becoming the culminating stages. Amid crises in the early twenty-first century, the value for educational theory of an artistic process that leads toward social justice in a democracy is emphasized.