Leading as a nursing dean/director is a golden opportunity to advance the discipline of nursing and delivery of healthcare. Stepping up from a nursing dean/director role is a difficult decision and lengthy process, whether under normal or cataclysmic circumstances. Although it might seem counterintuitive, best practice is to think about the end of dean/director role from the beginning and develop a tentative, appealing, and exciting plan for one’s next career move, including retirement. This chapter covers the uniqueness of the nursing dean/director role, what it takes to succeed, and hazards to side step as leadership journey unfolds. It presents the frameworks for understanding and navigating normative and cataclysmic role transitions. The chapter concludes with a section on best practices for transitioning out of the nursing dean/director role in both normative and cataclysmic contexts.