At the time social entrepreneurship gains momentum, youth organizations try to assume new roles: either by providing youth entrepreneurship trainings or by becoming ‘entrepreneurial’ themselves. However, these processes are not free of contradictions and unsolved tensions. The article highlights some dilemmas of the conventional discourses on social entrepreneurship in the frame of youth organizations. It argues that both youth work and social entrepreneurship stand for civic values and have long-term (and hard to measure) outcomes. Yet, they both create high expectations and share a bias towards what works. The article aims to provoke reflection and, thus, to broaden the theoretical array that shapes practice in youth organizations.