The phrase 'two worlds' is often used to describe the way in which political leaders in the Pacific Islands navigate and define their lives, and the different sets of societal norms to which they are subject. The capacity to move between 'worlds' is often central to their claims to leadership legitimacy and can be one of the reasons why they are ultimately chosen to lead. Through a comparative analysis of their published life histories, this paper explores the lives of the 20th-century Pacific's political leaders by capturing their experiences of growing up and out of colonialism, and what they did before they took up political office. They describe being significantly shaped by their relationships with educational and religious institutions, including with particular teachers and mentors, their experiences living and working overseas, and their vocational backgrounds, both religious and professional. The paper concludes that rather than 'two worlds' - often used as a metaphor for a larger historical narrative about modernisation and the passing of traditional way of life - life histories highlight the importance of multiple 'sites', 'spheres' or 'worlds' to our understanding of leaders life trajectories.