Given the increased heterogeneity characterising the transition from work to retirement, this study aimed to analyse the associations between different reasons for leaving the labour market and psychosocial wellbeing as a pensioner. The study was based on the so-called PSAE survey (Panel Survey of Ageing and the Elderly), which is a nationally representative survey of the living conditions of elderly people in Sweden. The results show that almost half of all pensioners cited health problems as a contributory cause for leaving working life. Furthermore, those who retired due to push factor reasons, such as health problems or labour market reasons, experienced a lower degree of psychosocial wellbeing than those who retired for other reasons. People who were able to influence the time of their retirement and those who were satisfied with their time of retirement experienced a better psychosocial wellbeing than those who had less chance to influence their retirement and those who were not satisfied with their retirement age.