This autoethnography describes the process of inquiry that led to the development of a series of ethnodramas that evoke teachers’ experience in the Chicago Public Schools (CPS). I discuss the methods I used to conduct a set of interviews with two groups of elementary school teachers in CPS: beginning teachers who had never worked a classroom as a full-time job and accomplished teachers who spent many years of their lives teaching students of color. I discuss the use of arts-based research methods to engage with these data, and I describe the interpretive journey I undertook as I wrote and produced ethnodramas about CPS teachers’ experience. A major dilemma for my analysis was communicating the structural inequalities that shaped the teachers’ narratives, particularly the Chicago system’s inability to create working conditions necessary to support the retention and professional development of teachers in the city’s high poverty schools. I describe how the conversation and inner dialogue generated by arts-based methods helped me recognize different patterns within the data, and inspired me to reframe my interpretation. In the conclusion, I discuss the limits of my approach as a researcher and an artist. Excerpts from two playscripts are woven throughout the article to convey the commitment that guided the teachers’ work and to evoke the social forces that shaped life in their classrooms.