The purpose of this study was to explore the perceived impact of critical reflection on my cultural competence and practice of culturally responsive caring as a high school choral director. Caring educators establish trusting relationships with students that support them as teachers in identifying their strengths and interests, then employ that knowledge to develop student-centric curricula that generate opportunities for student success (Gay, 2018; Hendricks, 2018; Noddings, 2012). This practice is what Geneva Gay (2018) termed culturally responsive teaching. Gay (2018) also asserted, however, that a teacher cannot not claim to nurture caring relationships without accompanying cultural awareness. Considering ongoing and increasing social and political tensions that lead to societal divides in the United States, educators could benefit from practicing awareness so they can facilitate learning environments in which students are challenged, courageous, and inspired to explore their identities in caring environments. The pursuit of such cultural awareness, competence, and humility demands ongoing, authentic critical reflection—a vulnerable and arduous practice (Howard, 2003). This autoethnographic study considers literature positing that caring relationships in education demand profound and intentional cultural competence. It explores critical reflection as a means for developing such competence. This is an in-depth investigation into my pursuit of a culturally responsive caring practice as a high school choral director and product of the community in which I teach. The implications of this study describe my “cultural experience as it is particularly—not generally—lived” (Adams, et al., 2015, p. 41). The resulting narrative may encourage further research and empower educators and teacher educators to commit to a similar critically reflective practice that can lead to an authentic practice of culturally responsive caring.