People start their career with certain ambitions, usually with a combination of professional and managerial targets in mind. While the majority fulfil some of their aims, only a few make it to a major leadership position. What it takes to make it to the top is still an unanswered question. To explore this question in a higher education context, we conducted 48 interviews with academics who became university presidents in the UK, France, and Vietnam. We identified individual factors such as career capital and institutional influences including organizational and cultural factors which together help explain their career success and career sustainability. Our study extends career capital theory beyond the three ways of knowing (know why, how and whom) by introducing the critical role of impression management for career development to the level of university president. Further, we found a lack of generalizability for boundaryless career theory in a non-Anglo-Saxon environment.