Music teacher educators are not alone when grappling with the challenge of preparing students to navigate diversity and confront inequity and injustice. Educators and researchers from multiple disciplines face similar challenges and have responded with various approaches related to cultural multiplicity. The concept of "cultural humility" is one such approach from the health sciences (Tervalon and Murray-García 1998). I both put forward and challenge cultural humility as a process for preparing music educators to think about, work, interact, and live with cultural multiplicity. I draw on personal experiences, using a critical autoethnographic epistolary to write letters between my various selves. Existing research on cultural humility is first organized into intrapersonal and interpersonal dimensions. I then problematize the virtuous reputation of humility specifically and explore its implications for cultural humility. I suggest that cultural humility is neither "good" nor "bad" but is something to be exercised differently in different contexts.