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This study solicited perspectives of underserved youth and educators who serve them regarding college and career readiness. We defined underserved youth as adolescents who experience inequitable access to educational resources. Purposeful sampling was used to select 84 focus group participants including educators and students (9–12th grade). Utilizing grounded theory analysis, focus group data revealed findings in three key categories. First, student and educator participants defined readiness as specific career knowledge and skills to develop concrete postschool plans. Second, both educators and students perceived limited availability of career preparation experiences as a barrier, while educators also provided examples of challenging life circumstances which deter youth from fully realizing their college and career potential. Third, educators and students reported that providing a broad array of career …