This article explores when it is appropriate for leaders to consider stepping down from their roles and passing the torch to new leadership. It examines signs that it may be time to transition based on research on leadership fatigue, stagnating vision, and succession planning. Specific factors discussed include declining health and enthusiasm from prolonged stress, an inability to drive innovative strategies, and having a capable successor prepared to take over. The article then outlines practical signs for leaders in industries like financial services, healthcare, technology, and non-profits that a transition should be considered. It provides examples of Microsoft CEO Satya Nadella and OWN founder Oprah Winfrey effectively navigating leadership successions. Finally, the article emphasizes the importance of succession planning, identifying the right time for an orderly transition, and ensuring the smooth handoff of leadership responsibilities to allow organizations to continue thriving under new vision and perspectives.