Abstract While literature about the relationship between well-being and accomplishment exists, previous studies were mainly quantitative and neglected the subjective experience of female retirees, which the current study aimed to address. Three female retired charity CEOs based in the United Kingdom were interviewed using in-depth, semi-structured interviews. The interpretative phenomenological analysis yielded 3 themes: (1) “accomplishment and well-being—a potentially negative interaction,” (2) “accomplishment and well-being—a positive link through interaction with other well-being domains,” and (3) “retirement—a moderator for negative direct impacts.” The results provided a complex picture of how high-achieving women postretirement perceived accomplishment as a contributor to their well-being. By highlighting an intricate link between accomplishment and other domains of well-being, particularly positive relationships, the findings critique that positive psychology overemphasizes the individual and highlight the need for further research into the interaction between different domains of well-being. The study also contributes to the debate about the relationship between age and well-being by illuminating the individuality of the experience depending on circumstances and environment. Finally, discussed are the implications of the current study in the context of retired high-fliers.