Since 2011, we have been working at an independent high school with a small group of teachers interested in studying their own teaching practices in ways that support both their individual and collective learning. The participating educators are engaged and challenged by their personal interests in deepening formative assessment practices while creating pedagogic practices that create classroom relevance for their students and themselves. For this paper, we have chosen to explore the self-study of one teacher's journey, in which he engages in the process of examining his own practices, biases, beliefs, and his changing relationships with students. We set the stage for the individual study by discussing the complexity of the interactions between the university faculty and the independent school educators.