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The purpose of this study was to examine perspectives of underserved youth, their families, and educators regarding college and career readiness. We used purposeful critical case sampling to select 103 focus group participants including educators, students, and parents/guardians from six school sites in two Western states in the US. Cross-case analysis of focus group data revealed that participants defined readiness as specific career knowledge and skills and the ability to develop concrete actionable post-school plans. Based on stakeholder perspectives, we also found that providing a broad array of career related learning and exploration activities, coupled with the presence of trusted adults who can serve as mentors and guides, can create capacity for youth to expand career options and post-secondary opportunities.