Many teachers enter the profession through alternative certification programs, completing a master's degree at the same time as they start their teaching careers. This study explores the teaching and graduate experience of one of these teachers. In this collaborative inquiry, this teacher was both participant and co-researcher with two teacher educators. The themes of School Dysfunction, Culture Clash, Disconnect between Coursework and Teaching, and Authenticity emerged through the study of the teacher's work. These findings led to the conclusion that students' experience of teaching needs to be brought into graduate classrooms and treated as valuable knowledge. If new teachers are given opportunities to openly and more authentically confront the disconnections they experience in their teaching and academic work, they may be more able to find meaningful ways to navigate the complexity of teaching and change within schools.