This dissertation explains why people work in lousy jobs in the private security industry, as illustrated by a case study of this work in Ontario, Canada. This industry has experienced rapid growth worldwide for decades and is a significant and intrusive part of many lives. Private security worker jobs are precarious, usually poorly paid, offer few benefits and require long and erratic hours. It is a lousy job that requires both endurance and skill. The workers have less public respect and fewer resources available than the police, yet the industry has few problems attracting many workers. Some of these workers develop a solid attachment to the industry and strong emotional engagement with the work. Their attachment to the industry is strongly associated with specific ideas and practices of masculinity and this helps explain the continued dominance of men at all levels. They also engage in specific forms of emotional labour that helps give them feelings of self-worth about their role in protecting people from threats such as accidents, acts of violence, and loss of property. This combination helps perpetuate a specifically masculine concept of providing security. Using ethnographic methods and phenomenological analysis, I show how workers practice gender in the workplace and how the emotional labour required by their job discourages some people from working in the industry and attracts other. The resulting industry practices help formulate unique practices and ideas of security that are gendered, racialized and relevant on a global level. The industry's expansion deepens and expands the social understandings of security in contemporary society as a masculine project and this project shows how that occurs at the level of individual workers in the field.