The purpose of this investigation is to deepen understanding of the clandestine professional lives of men who care for young children, exploring the pressure to hide parts of themselves experienced by many. The author utilizes an autoethnographic approach to examine social and psychological experiences he has navigated during his work as a classroom teacher, counselor, and researcher in urban Head Start centers. He finds that there are structural, attitudinal, social, and conceptual barriers to men being engaged in young children’s lives as educators and caregivers. In response, the author considers how dominant theories of caregiving in the field of early childhood education are informed by and inadvertently perpetuate traditional hegemonic notions of masculinity. He concludes by articulating the importance of critical praxis and disrupting hegemony, re-imagining opportunities for transformation and resilience. (author abstract)