This article examines the employment perspective of older workers in Germany (prospectively). It considers the reasons for leaving employment among those who take early retirement, or those who receive a disability pension (retrospectively). The data is taken from the 4th wave of the representative lidA-Study in 2022/2023 ( www.lida-studie.de ). The results indicate that most of the baby boomer generation (born in 1959 and 1965) would like to retire early, long before reaching their official retirement age and long before the point in time at which they believed they could continue working. At the same time, a small portion of the subsequent generation (those born in 1971), seems to be preparing themselves for a somewhat longer working life. The reasons for the preferred early retirement are mainly related to a desire for self-determination in life, followed by stressful work and health problems. In all three birth cohorts, there is a widespread willingness to remain in employment longer than currently desired under certain circumstances—particularly if individuals were given more influence over how their work is organised. The retrospective survey data shows that the desire for self-determination also dominates the reasons for early retirement of those who have already left the workforce. In contrast, for those who have transitioned to a disability pension, demanding work is the primary factor in addition to health problems. A key conclusion is that if politics and economy want to keep older employees in the workforce for longer, they must find ways to make them want to work longer. This cannot be achieved without a fundamental consideration of working conditions.