Divorce is increasingly common and can have a significant impact on later-life work and retirement. However, the lived experience of choice and control around divorce and its financial ramifications is not adequately understood. This article demonstrates how women and men differentially experience divorce as a long-run lifecourse factor, which can impact an individual’s scope for choice and control about working in later life, and how and when to retire. From a dataset of 47 in-depth interviews of workers aged over 50 in the United Kingdom from the international Dynamics of Accumulated Inequalities for Seniors in Employment project, findings show that the extent of choice and control at the time of divorce was constrained by individual and gendered lifecourse factors, by gendered, asymmetrical access to salient financial information and by emotional responses to relationship breakdown. Drawing on cumulative (dis)advantage over the lifecourse as a theoretical lens, this article demonstrates the ways in which short-term choices reinforce existing gendered and socio-economic (dis)advantage while instigating new pathways for (dis)advantage that have long-term implications for work and retirement.