Social enterprises offer the promise of financially sustainable organizations that can respond to the world's most pressing problems. Yet for social enterprises to succeed, their leaders must effectively manage conflicting demands that arise from dual commitments to improving social welfare and achieving commercial viability. While existing research highlights distinct skills for enabling social missions or for achieving business outcomes, we draw on paradox research to build theory about the challenges and associated skills for effectively managing the tensions emerging from the juxtaposition of social mission and business outcomes. We then use two exemplary settings for educating social entrepreneurs, one in the classroom and one in the field, to illustrate pedagogical tools for teaching these skills. Integrating these challenges, skills, and pedagogical tools, we propose a paradoxical leadership model for social entrepreneurs.