Structural barriers beyond academics might explain why academic interventions have not significantly increased the representation of historically underrepresented groups in STEM fields. For the past 20 years, the Saturday Academy (SA), a STEM partnership between a university, a community college, and an urban school district, has embraced a holistic approach to academic enrichment. We report alumni perspectives on how SAs affected their professional paths. An 88-item retrospective survey focused on career literacy, personal development, socioemotional learning, and resource access was administered through a private Facebook group and completed by 96 alumni. Descriptive statistics were used to estimate effect sizes, identify patterns, and generate insights into participants’ perspectives. The largest shifts were noted for self-efficacy, professional network development, and relationship development. Moreover, those reporting lower baseline career literacy, personal development, or resource access reported the greatest improvements after SA. Program design recommendations and study limitations are discussed.