In this conversation with EdUp Provost host Dr. Gregor Thuswaldner, Dr. Kathy E. Johnson and Dr. Beth Ingram discuss their chapter “Seasons of a Provost” in  The Chief Academic Officer's Handbook: A Provost’s Guide for Visionary Leadership (Johns Hopkins University Press, 2025). They explore the often-overlooked topic of provost career transitions, the importance of aligning with presidential vision, and the necessity of having a plan B for unexpected changes. They also delve into the dynamics of cabinet relationships, fostering faculty relations, and the reflective practices that can guide provosts in assessing their career paths. The conversation concludes with personal reflections on knowing when to stay or go in one's career and book recommendations that emphasize empathy and understanding in leadership. Takeaways: Provosts often operate in the background compared to presidents. Career transitions for provosts are rarely discussed openly. Aligning with the president's vision is crucial for provosts. Having a plan B is essential due to high turnover rates. Building a network of support can provide valuable insights.