Objective: Despite significant attention from federal and state policy makers, postsecondary completion rates in the United States remain stratified across race and socioeconomic background. This study examines a community-based college readiness program for underrepresented students from low-resource neighborhoods in Chicago, Illinois. Method: This qualitative study utilized validation theory to consider the experiences of program participants. During the Summer of 2014, I collected data through six focus groups with participants who successfully completed the college readiness program between 2010 and 2014. Results: Aligning with phrases from Chicago poet and activist Gwendolyn Brooks, I describe major themes that reflect the validating experiences of program participants. Overall, participants indicate that program experiences affirmed existing motivations that drive postsecondary aspirations and persistence. Participants felt most when their existing strengths were consistently recognized as an important factor for college transitions. Contributions: Findings offers further evidence for the critical role of validation in supporting the postsecondary pursuits among students from underrepresented backgrounds. Participant insights also offer critical observations about unintended consequences when successful programs grow rapidly to satisfy external constituents.