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This paper identifies and describes the experiences of three women who navigated personal and professional loss as they transitioned from teachers into assistant principals (APs) at two large, suburban schools in the South. Using poetic methodology to explore and present the stories of these new leaders, this study sought to illuminate the intense challenges women contend with during their first years in formal school leadership. In an effort to disrupt the sexist assumptions of what preparation and professional development should look like for leaders in their novice years, this study speaks to the often hidden and minimized struggles women contend with as they pursue growth and greater influence within a school.