This chapter revisits the Expert Transition Cycle presented in Chapter 3 from the perspective of how identity changes. Five stages of the Expert Transition Cycle operate during transition. Intention orients and clarifies choices and provides drive. Inquiry holds open the transition process with criteria for choice and discrimination based upon intention. Exploration actively investigates the familiar and the new elements of identity, roles, social situations, work opportunities, beliefs, and performance. Commitment narrows and targets the choices made regarding those elements. Integration modifies and adapts the identity to include new elements, knowledge, experience, and beliefs. Each stage of the Expert Transition Cycle is reviewed in light of the operation of the transition experiences, such as cognitive flexibility and purpose. This is discussed in light of the retrospective interviews with twenty-four elite performers in three domains (business, sports, and music) who successfully and repeatedly transitioned to higher positions within their field.