This article explores the dynamic structures of emotions used by former urban teachers as they negotiated the challenges of the profession. Drawing from a national sample of 25 former urban teachers, this article looks closely at the lives of two teachers who taught in urban intensive school districts. Specifically, the piece captures the emotional aftermath of leaving teaching around two themes: (a) recognition of guilt and (b) continued advocacy for their students. We found that teacher leavers continue to struggle emotionally with their choice to leave the classroom while remaining committed to affecting change in the educational system.