Gender research in organizational behavior has primarily focused on understanding and addressing the disadvantages women face in masculine work environments. While this body of work has been essential to understanding gender inequality in the workplace, it has left a critical gap: examining how masculinity both shapes and constrains men’s experiences and outcomes. This paper reverses the traditional focus of gender research in organizational behavior by arguing that masculinity is not only a source of advantage; it is also a system of traits, expectations, and values that imposes psychological and social costs on men. Drawing from interdisciplinary research across organizational behavior, psychology, and sociology, we argue that aspects of masculinity—such as stoicism, risk-taking, aggression, self-reliance, ambition, and dominance—are simultaneously organizationally rewarded as well as personally harmful. These expectations contribute to men’s poorer mental health, weaker social support networks, higher rates of self-harm, and greater exposure to physical danger. Moreover, while these aspects of masculinity are thought to drive organizational and societal growth, success, and power, they can also produce exclusionary cultures that undermine employee well-being. This paper argues that gender equity efforts must account for how masculinity shapes men—not only in the ways it enables their power but also in the ways it restricts their well-being. Addressing the double-edged nature of masculinity is not a diversion from gender progress but rather is an essential step toward creating healthier individuals, organizations, and societies.