Stemming from my personal encounter with what I consider a racial affliction imposed by a White female teacher, I provide a glimpse of my racial narrative as a young Black male to illustrate a reference point for thinking through how racism functions in homes and schools. It touches on the importance of race-based conversations within school and out of school spaces. In this article, I illustrate the creation of a "critical" relationship between parents, youth, and educators in that I used a critical family book club as a mechanism for engaging parents and students in discussions about race and racism. Drawing from interviews, memos, field notes, and other forms of research data, I analyze participants' experiences with race, racism, and power. I conclude with the pedagogical possibilities of enacting critical race pedagogy and critical family book clubs in K-12 spaces.