This study examines life courses and retirement adjustment in the Netherlands. Gender-split latent class analyses identify four distinct trajectories among men and women, covering life events in work, family, health, care, and volunteering. The largest trajectories indicate traditional male and female life courses. Compared to those with traditional male trajectories, men with lifelong volunteering adjust better to retirement, financially, socially, and psychologically. Despite family and health issues, men making careers through mobility miss the prestige of work less, but men with late-career mobility are similar to the reference group. Women combining work with care and volunteering adjust better to retirement, missing work-related income, prestige, and role fulfillment less, while work-oriented carers do not differ from women with traditional female trajectories. However, mothers re-entering employment after childcare face financial challenges in retirement. These findings highlight gender differences in life courses and support the dynamic resource perspective on retirement adjustment.