The authors examined how middle and high school students participating in a literacy-and-songwriting initiative in Detroit, Michigan, experienced moments of possibility that supported the youth in envisioning themselves as college bound. The authors explain how they drew from culturally relevant and sustaining educational approaches to design literacy instruction for youth of color that built from students' interests as strengths, challenging educational disparities related to college readiness and access. The authors describe three workshops that they facilitated with youth participants, examine and share examples of multimodal artifacts generated by youth participants during the workshops, and provide recommendations for adolescent and adult literacy educators seeking to enact similar approaches for supporting students' college readiness in their own work.