In this chapter, we analyze new global challenges to youth employment, as well as the emerging opportunities for addressing the school-to-work transition for youth and empowering youth with the skills for social entrepreneurship. Globalization, migration, and mobility present new challenges and opportunities for youth to generate sustainable livelihoods. To address the challenges of youth unemployment globally, we argue there is a need to look beyond mere policy reforms and instead to actual programmatic interventions that directly try to assist youth to create and access livelihood opportunities. Specifically, we assess whether life skills training programs can provide an innovative approach in the education-to-work transition, and as such develop a unique condition for effecting productive and sustainable change in education globally. Life skills programs can enable youth to be architects of social change and to actively create opportunities to generate livelihoods.