Decisions around retirement and continued labor market participation are of great significance for those who make them, as well as policy makers, researchers, welfare states, and pension programs. The literature acknowledges the multifaceted nature of these choices and particularly the interaction of key variables—job satisfaction, financial status, caring responsibilities, spouse’s plans, and health. This article explores this latter factor, challenging assumptions that it can be treated as an unproblematic independent variable. Analyzing qualitative data from interviews with 96 people approaching or in the midst of retirement, the subjective experience of health and its effect on decisions was strongly evident. The socialized context—as shaped at societal, organizational, household, and individual-life-historical levels—was crucial in understanding how similar symptoms of morbidity resulted in widely varying decisions/outcomes. Direct interpersonal experiences, shaped by social structures, were useful in explaining the prevalence of health pessimism, despite general increases in life expectancy.