In this exchange between an EdD professor and one of their practitioner-scholars, the two recount their respective and overlapping journeys in Critical Social Theories for Just Schools and Communities. While the professor was trained as a philosopher and has embraced the theoretical throughout her career, the practitioner-scholar enrolled in the class with much skepticism about the usefulness of theories, especially coupled with the word "critical" in our politically divisive society. They share the educational unfolding that occurred for both of them as they navigated various challenges of infusing theory into a practitioner-based educational doctoral program. The professor offers insights into their pedagogical strategies when presenting sometimes contentious topics, and the practitioner-scholar provides an honest unveiling of their self-awareness.