The purpose of this study was to solicit perspectives of underserved youth and educators who serve them regarding college and career readiness. In this study, underserved youth refers to adolescents who experience inequitable access to educational resources. Purposeful sampling was used to select 84 focus group participants including educators and high school students (9-12th grade). Utilizing grounded theory analysis, focus group data revealed findings in three key categories. First, participants defined readiness as specific career knowledge and skills to develop concrete actionable post-school plans. Second, perceived barriers such as limited availability of career preparation experiences and challenging life circumstances combined to deter youth from fully realizing their college and career potential. Third, providing a broad array of career related learning activities, coupled with the presence of trusted adults who serve as mentors and guides, can create capacity for young people to expand career options and postsecondary opportunities. [This is the online version of an article published in "Youth & Society." For the final published version of this article, see EJ1328865.]