Women in the fields of medicine and science often consider career pivots to transition out or transition up; in this review, we offer 4 lessons learned to make those pivots maximally successful. These lessons emphasize the need to honor the feeling that it is time to pivot, especially if you develop a strong sense of restlessness indicating you are in a space that no longer serves you; they also emphasize the importance of seeking the guidance of a mentor, sponsor, or coach. Although flexibility is a substantial part of the transition, it is important to have a road map in the form of a career development plan, and it is of utmost importance to complete the transition professionally.