This conceptual analysis examines the implementation of a state-funded college and career readiness pilot program at a small, rural all-Black school in Illinois. Drawing from ethnographic data that dates from 2010, I offer a retrospective analysis on individual based intervention programming for college and career readiness. Concerned with how young Black high school students are constructed as problems in regards to increasing readiness, I trace policy failure through the theoretical lenses of deficit ideology (Valencia in The evolution of deficit thinking: educational thought and practice, Routledge, New York, 1997) and dysconscious racism (King in J Negro Educ 60(2):133-146, 1991). This analysis illuminates how racism ultimately undermines a-contextual efforts to increase readiness for college and career.