This chapter explores the complexities of switching institutions for career advancement in academic medicine, drawing on the lived experiences of a seasoned LHS+ professional who navigated multiple transitions across diverse settings. From starting in rural clinical practice to assuming leadership roles in academic medicine and diversity, equity, and inclusion (DEI) initiatives, the narrative highlights both the challenges and opportunities inherent in such career shifts. Key lessons emphasize the importance of self-awareness, adaptability, and intentionality when considering institutional changes. “Restlessness” emerges as a recurring theme—serving as both a catalyst for personal and professional growth and a motivator to seek environments that better align with evolving aspirations. The chapter details inhibitors of success, such as misaligned institutional priorities, and catalysts, including personal calls to action and the desire for meaningful impact. Ultimately, it equips readers with better practices for navigating transitions, such as contract negotiation, documenting commitments, and identifying allies early. Through reflective insights, it provides a roadmap for leveraging institutional changes to enhance career satisfaction and impact, fostering resilience, and success in academic medicine.