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Transitioning from a leadership position (eg, chair, chief, director, dean, executive officer) at an academic health center can be both challenging and, when done successfully, rewarding to all concerned. Successful transitions require that the leader carefully consider why they may want (or need) to make a change, define when is the best time to leave, and plan how their transition is made. Leaders may leave their positions for numerous reasons, including attractive new opportunities and experiences, problematic issues in their current role, completion of their term, unplanned termination, and dismissal. It is prudent for leaders at the outset of their position to anticipate and plan for their eventual transition. To determine when and how to transition, leaders should consider their personal satisfaction, their professional development, and the potential effects on the people, programs, and units they lead. Considering a career move requires appropriate assessment of personal and professional factors plus substantial self-awareness, as well as candid advice and assistance from others. Effective leaders understand when they have served for too long or too short a time and when it is best to move on in the interests of those they serve as well as their own career development. It is important for both the leader and the organization to ensure that the leadership transition process is smooth and well organized, with appropriate planning and communications. Knowing why, when, and how best to move on from one's leadership position can open new career opportunities, enhance one's legacy, and provide satisfaction in what the leader and others have accomplished.