Intergenerational poverty and scarce financial resources can create and sustain detrimental behaviors and outcomes among adolescents. Efforts to increase financial literacy and job-related skills, however, can offer youth from low-income households knowledge, skills, and opportunities otherwise unavailable to them. Targeted interventions that combine financial literacy and job-readiness components may help adolescents disrupt the cycle of intergenerational poverty by increasing economic awareness, adaptive financial behaviors, and work-related skills. Drawing on career construction and asset theory, the present study examined changes in financial knowledge and labor skills among youth from low-income households (N = 111) over the course of their participation in the Road to Success curriculum as well as how changes varied across demographic characteristics of participants. Data analysis included descriptive statistics, t-test analyses, and MANCOVA. Results indicated several improvements from Wave 1 to Wave 2 as students developed job-readiness and financial literacy knowledge. Potential educational and policy implications are discussed.