When a new superintendent is hired, Tom Thompson, middle school principal, is squeezed between complying with the demands of the district and cultivating a positive culture in his school. He wrestles with the stress of facing tough leadership choices that take a toll on his physical and mental health. Tom realizes that a career-ending move might result from a miscalculation of available options. This case discusses the role of the principal in the district hierarchy, the impact on school staff resulting from punitive district personnel policies, the development of relationships with a new supervisor, and the ethics of test administration underlying administrative decision making.