This paper, by Metcalf Foundation Innovation Fellow Pat Thompson, explores illuminates the crucial role that reflective conversations can play in uncorking creativity and inoculating us from workplace stress. More than 150 leaders in the arts, environment, and community sectors share their reflection on what these times are asking of nonprofit leaders and their organizations. It unpacks learnings on such varied themes as: how we define leaders; what makes work meaningful; the power of emotion in shaping organizational culture and driving change; challenging conventional thinking related to layoffs or terminations; and, how architecture and physical space shape the nonprofit sector and its work.