This study examined resilient men in higher education administration, educational leadership programs to determine how they identified components of their resiliency, how they described events that demonstrated their resiliency, and how they prescribed ways in which preparation programs can foster resiliency in students. Using masculinity theoretical lenses, our findings showed male leaders defining their resiliency in varied gendered terms but describing a range of acting as leader bounded. Through their privilege, men have ironically been the ones to design social constraints, undoubtedly their own oppression. (Contains 1 table.)