There is a gap in research about the gender identity and gender experience of men leading all-boys middle-schools. In addition, there has been little work done exploring the link between the inner lives of male school leaders, their level of burnout or satisfaction, and the impacts on their school leadership. The purpose of this study was to explore how male middle school directors of all-boys' middle schools make sense of, engage with, and are impacted by their masculinity. The study employed narrative research with a social constructivist and post structural feminist lens. Four participants completed digital participatory journals, written document analysis of school communications, and semi structured interviews. One participant was selected as a critical case for site visits and nonparticipant observation. Study findings suggested that participants' gender development was characterized by limiting patriarchal beliefs in early life, destabilizing gender experiences, new ways of knowing and being, and ranges of continued engagement with gender identity. Through their inner, interpersonal, and institutional work focused on identity and meaning-making, the male leaders of the study have healed their childhood wounds, applied their discoveries to their leadership practice, and modeled a liberating existence for the men and boys in their care. The leaders, however, did not demonstrate or report consistent, effective strategies to maintain life balance or support their health and stress response. In addition, their masculine identity revealed an insufficient range of awareness and commitments towards issues of gender equity and feminism in their work. Key recommendations include the effective deployment of personal sustainability and wellness practices considerate of male worldviews and the need for continued education for male leaders in gender allyship and gender equitable leadership practices. Areas for further study may include broadening the scope of gender exploration inside boys' middle schools to include the feminine standpoint or a wider range of masculinities and sexualities. Further research could specifically address the inconsistency of self-care practices and the correlation to masculine beliefs and expression by male leaders in single-sex schools. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]