This study investigates the transition to retirement of male academics. It applies approaches drawn from Cumulative Advantage and Disadvantage (CAD) principles to expand Continuity theory by examining evidence for continuity and inequalities in the lifestyles of the respondents. Biographical-Narrative interviews with 20 retired academics in Brazil and the United Kingdom were conducted and analysed using Thematic Analysis. An exploration of the same occupational group in different cultural and social contexts was carried out to capture a diversity of CAD influences on retirement outcomes. The experience of continuity was individualised to each participant due to their unique combination of advantages, and their subjective interpretation of their experiences. Cumulative processes identified in this study related to (1) occupational roles played in their career; and (2) organisational level policies and practices for retirement. At the level of individual retired men, cultural and social context factors were not perceived as influential in the achievement of continuity in retirement. Continuity theory is still supported, but alone offers limited explanations of the diversity of experiences in the transition to retirement of male academics. A consideration of the role of cumulative processes and systemic dynamics, including how individuals respond to their experiences in retirement, shows how these different factors interact and affect retirement and ageing. Further studies should investigate the processes identified with other occupations, as well as women and minority groups.