This chapter asserts the imperative of diversified earning strategies in youth skills training to bolster income access, economic participation, and alleviate unemployment in Kenya. Despite declining youth employment rates due to high graduation levels and socioeconomic barriers, initiatives like CAP-Youth Empowerment Institute (CAP-YEI) have implemented Basic Employability Skills Training (BEST) to address these challenges. Drawing from rigorous longitudinal project evaluations, summative assessments, and internal monitoring, the chapter examines the efficacy of multiple earning strategies for youth livelihoods. It succinctly outlines current obstacles faced by Kenyan youth in workforce integration and CAP-YEI’s responsive interventions. Furthermore, it explores how youth leverage diverse earning strategies to enhance their economic resilience. The chapter concludes by urging researchers and practitioners to further integrate and scale these strategies within the skills training sector to optimise outcomes and empower youth for a prosperous future.