In this paper, we describe pivotal experiences that have shaped our respective professional journeys when teaching action research. We situate these experiences in relation to how they have contributed to our collective living theory of practice. This discussion unfolded as we explored ways to improve our own practices and the practices of our students. We conclude that this and similar questions can only be authentically answered when we as practitioners and faculty in higher education settings are willing to interrogate the contexts within which we interact and the complex intersections between our own intentional practices and selves and our students’ willingness to engage in critical discourse.