Discussion around gender differences and inequality is fervent in both public and academic settings. This project presents and analyzes the process of coming to understand what it means to be a man in the current social climate by focusing on the experience of a single individual, that of the researcher. Using the qualitative method of autoethnography, this project involved creating and analyzing textual accounts of moments that were impactful to the development of masculine identity during the formative years in late adolescence and early adulthood. An analysis of those passages was conducted using a lens informed by feminist, critical, and social learning theories to extrapolate qualitative data pertaining to socio-cultural factors involved in gendered identity development. The analysis revealed social messages originating from a variety of sources, including parents, strangers, authority figures, friends, adversaries, and romantic interests. Messages took many forms ranging from subtle to overt. Qualities of these messages were identified and examined to identify the impacts of the messages on my overall sense of self, followed by a discussion about how various diversity factors may have influenced how my masculine identity emerged. The project concludes by proposing a more nuanced view of masculinity, including a call for distinction between hegemonic, traditional, and positive masculinity; an emphasis on balance; and an appeal to working toward inclusive discourse around gender.