As products of negotiations, union contracts provide insight into areas of stress concerning work hours and schedules. Our analysis demonstrates the ways workers in two occupations—nurses and firefighters—use collective bargaining to develop workplace policies that enable them to manage jobs and family. The contracts show significant differences between firefighters and nurses over issues of work scheduling, overtime, and vacations. These differences reflect nurses’ concern with putting boundaries on their work lives in favor of caregiving and firefighters’ concern with bread winning. Nurse contracts specify scheduling rules in detail, heavily restrict mandatory overtime, and outline guidelines for distributing prime time vacations. Firefighter contracts, by contrast, downplay the substance of scheduling processes in favor of emphasizing fairness among firefighters in the context of restrictive weekly schedules and equal access to overtime opportunities. Findings suggest not only that union contracts are an important tool with which workers manage the competing demands of work and family, but that the manner and extent to which such negotiations happen are shaped by gendered occupation.