Navigating a surgical career involves not only technical skills but also the ability to recognize when a workplace no longer serves your growth and well-being. Knowing when to leave a place requires self-awareness, strategic thinking, and the courage to make a change. This chapter explores key indicators that signal it may be time to move on, the role of mentors and allies in decision-making, strategies for navigating unsafe environments, and how to transition effectively into a better professional setting. By leveraging mentorship, protecting yourself in difficult situations, and learning from adversity, you can ensure each career move aligns with your professional values and aspirations.