<p>The retirement age receives increasing attention in times of population ageing. Researchers and policymakers argue that working lives have to be extended to balance out the demographic shift. The preferred retirement age highlights the perspective of the individuals regarding this issue, underlining when they themselves would best like to leave the workforce and enter retirement. Previous research established that employees prefer to retire earlier than self-employed individuals. This article contributes to understanding why this difference in the preferred retirement age exists. It suggests that both groups differ not only in their characteristics but also in their behaviours. A&#xa0;multilevel analysis of microlevel data from the European Social Survey has been carried out, and findings show that poor health can lead employees, but not the self-employed, to wish for an earlier retirement. Moreover, they show that the state pension age influences the preferred retirement age of the self-employed more strongly than it does that of employees. The findings suggest that employees and the self-employed take different perspectives on retirement, approaching it with different logics. Because retirement is a&#xa0;common marker for the onset of old age, the findings also suggest that employees and the self-employed approach old age with different logics. Researchers should consider this qualitative difference in their future studies on the preferred retirement age and on the concept of old age. Policymakers can use the findings to refine their efforts to extend working lives.</p>