This session will discuss how fellowship programs can help to build diverse and tangible skills that complement what PhD students learn through their academic training. Such extramural programs can effectively supplement their support of advanced research by fostering leadership and team skills. Moreover, innovative project-based programs can provide a better understanding of how to navigate and flourish in a variety of organizational structures beyond the ones usually encountered in graduate school. In addition to fostering valuable institutional and operational experiences, extra-academic training through fellowships can include project management, budget, and personnel management skills that are invaluable both within and outside the academy. By encouraging students to explore diverse career opportunities, mentors can help early-career humanists envision a more permeable academy, broaden the impact of their work, and lessen the inevitable anxieties that accompany a perennially tight academic job market. The panelists will share the diverse programming they have developed through their scholarly and fellowship programs. They will also draw on their own experiences to discuss how PhDs can develop realistic understandings of the benefits and drawbacks of different career paths by engaging with practitioners in various fields.