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This analysis focuses on the ways that Ms. River, a Black woman in her first year of teaching, utilized a culturally relevant approach to a college/career readiness course to affirm and critically engage middle school Youth of Color. This paper utilizes poetic analysis derived from an ethnographic study investigating the experiences of early career teachers navigating politically restrictive contexts for teaching to explore the ways that Ms. River drew upon her racial identity and previous professional experiences as she re-envisioned college and career readiness. Study findings focus on her disruption of white-centric definitions of college and career readiness focused on skill acquisition and inclusion of opportunities to explore power within career fields and their lives.