This study embraces the lived inquiry of artists/researchers/teachers termed a/r/tography. In doing so, it recaps the journey of five art educators, their first memory of art related experiences, paths to art education, and teaching. Topics of collaborative conversations were examined in relationship to theoretical ideas of Eisner and Dewey and the broad educational goals for twenty-first century high school students. Teachers in this study have had extensive experience as leaders in multiple arts curriculum movements across time and programs. They thought about art content to examine their own experiences. Ideas that surfaced were tested against their own practice, evidence provided by high school students, their students’ artwork, and historical art references. Analysis of documented conversations resulted in the emergence of the following key themes: (1) Our experience influences and lives on in our beliefs, understandings, and decision making for our classrooms; (2) Conversations can provide a stimulus for reflection when they are focused, guided by emerging questions, and invite diverse perspectives and experiences; (3) Assertions about the kind of thinking the arts employ invite ambiguity in understanding and seem disconnected to art education practice; and (4) A curriculum that addresses abstract concepts and thinking skills that invite student engagement in inquiry, learning, and being awake to possibilities is needed in art classrooms.