The purpose of this study was to explore the remembered experiences and perspectives of closeted and semicloseted queer school administrators who lived and worked in a community that did not support or embrace sexual diversity. The analysis of data, gathered through semistructured interviews, revealed that these administrators continually search for clues to define the margin of tolerance for queers in their schools while constantly negotiating their identities in order to fit. For participants in this study, the challenge of leading a school community was ultimately a labor of love and fear, given that these professionals enjoy a different and lesser set of civil rights than their nonqueer counterparts because of the sacrifices that the former make to maintain their job security. (Contains 1 table and 6 footnotes.)