This article reports the collaborative self-study of a teacher educator and two teacher candidates, focusing on the unforeseen negativity of experiences encountered by the three researchers in both a university methods course and student teaching settings. The implication of this study helped the researchers foresee new hypothetical learning trajectories for their respective students. Throughout the study, the university teacher educator and two teacher candidates tried to maintain a collegial relationship while analyzing their teaching and learning experiences. The researchers analyzed the effectiveness of their mathematics teaching strategies over an extended period of time. The changing roles of the researchers throughout the study encouraged them to examine not only their own teaching processes but also those of the other researchers. As critical colleagues they positioned themselves in different contexts. This study generates several insights for the improvement of the researchers' future teaching practices. The results suggest that collaborative self-study by a teacher educator and teacher candidates can generate effective learning experiences for all participants. (Contains 1 table.)