Critical thinking remains a challenge for students even at the undergraduate level. In this article, I describes how he utilized the tenets of self-study to explore introducing critical thinking instructional strategies to preservice teachers. Frustrated and curious, I attempted to better understand the group's reluctance to using these methods with their own elementary students during internship. To collect and triangulate my data, I asked the preservice teachers to respond to weekly electronic surveys, engaged in focus groups with them, kept reflection notes, and presented his dilemmas and findings to colleagues. Using a narrative analytical process, I uncovered assumptions that affected my relationship and results with the teachers and questioned identities held by himself and the preservice teachers as possibly being unhealthy. The need to consider how the instruction of critical thinking is presented to preservice teachers as well as studying ways to support positive, empowering identify formation in emerging teachers is discussed.