This article reviews the effects of year-round schooling on administrators. It discusses that year-round schedules provide shorter breaks between academic years, so principals have little to no actual vacation time since they spend breaks planning for the upcoming school year. This can lead to burnout of administrators. It also identifies three different year-round schedules and notes that year-round schooling is adopted to house more students, potentially improve achievement for disadvantaged students, and save money, though cost reductions may be minimal in extreme climates. The article questions whether disadvantages of longer school years outweigh advantages and considers effects on all stakeholders.