This research studies how 24 experts in sport, music, and business were able to make successful and repeated career transitions to senior levels in their field. It examined – among other aspects – the roles of cognitive flexibility, personal intelligence, generative thinking, motivation, and contextual intelligence in career transitions. It also examined how identity changes and adapts during a career transition and how self concept evolves over the course of a career. In-depth interviews were analysed both qualitatively and quantitatively and served as the basis for evaluating several theories of expertise, cognition, motivation, and intelligence. Key findings include: deliberate practice was rarely mentioned as a contributor to transitions; the early development of expertise in multiple domains contributed to its generalizability; transition expertise evolved over the course of a career; and self concept did not unfold in a linear progression of sequential stages as predicted by many theories in the field.