Given the increased heterogeneity of the transition from work to retirement, this study aimed to analyse the associations between different reasons for retirement and psychosocial wellbeing as a pensioner. The study used data from the Swedish Panel Survey of Ageing and the Elderly (PSAE), a nationally representative survey of the living conditions of older people in Sweden. The results show that almost one-half of all pensioners cited health problems as a contributory reason for ceasing work. Furthermore, those who retired for ‘push’ reasons, such as health problems or labour market factors, experienced lower psychosocial wellbeing than those who retired for other reasons. Moreover, the results show that those who were able to influence the time of their retirement enjoyed better psychosocial wellbeing than those who had little or no opportunity to do so. This was true when controlling for other factors relevant to the wellbeing of pensioners. The results lend support to the argument that, if a man's retirement is instigated because his skills are no longer required, there will be a decidedly negative effect on his wellbeing – and that this effect is stronger than the equivalent impact on a woman's wellbeing. In relation to previous findings in this field, the results make it clear that retirement is far from a uniform process or state.