Gay men in sport are currently at a historic crossroads. On the one hand, the sport industry has never been more accepting and inclusive of sexual minorities than it is today. On the other hand, however, the sociocultural norms and organizational practices within sport that have traditionally stigmatized gay men and influenced their career choices—both in pursuit of and persistence within careers in sport—continue to exist. Drawing from life course theory, the purpose of this study was to qualitatively explore the experiences of 12 gay men working in the sport industry and understand how their awareness (or lack thereof) of the stigma associated with being gay shaped their career decisions. Findings suggest that historical/social context, organizational practices, personal and professional relationships, and the interplay between these factors inform how gay men navigate their stigmatized identities while working in sport.