This article uses two narrative portraits of early career teachers to examine the central role of principals in influencing teachers’ feelings of personal and professional well-being, with both negative and positive effects reported. The portraits of two female early career teachers illustrate the vulnerability of many beginning teachers, whose work conditions are dependent on the goodwill and discretion of colleagues and leaders. In both stories, the principals played a central role in terms of the amount and kind of personal support they gave and their leadership in developing the overall school culture.