This article is written from the experiential and theoretical perspectives that I encountered as a Black female public school educator who, after twenty-plus years of public school teaching and administrative experiences, became an assistant professor at a predominately White research university. Being a student of critical race theory, I write this experience narrative from the perspective of life notes in order to help "demystify[ing] African American feminist ways of knowing, in moments of reflection, relation, and resistance" (Dillard, 2003, p. 135). Moreover, this article represents an " endarkened feminist epistemology" (Dillard, 2003) in order to shed light on how incidents and events with race, class, and gender translate into meaning for both of my professional careers and my life in general. A chronologic comparison of my experiences in both careers reveals the debilitating affects of race and gender. By sharing this experience, I hope that all who are involved in the recruitment, retention, and promotion of women and minorities in these professions (public school administration and the academy) will better understand how acts of racism and sexism create distractions that hinder their success in these careers.