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Objective: Although previous studies of shorter duration have identified numerous risks and protective factors that powerfully influence outcomes in young adulthood and midlife, this long-term prospective study examines the effect of these prognostic factors on age at retirement and satisfaction with retirement. Method: In this prospective study, a cohort of socially disadvantaged men (N=151) were followed from adolescence until a mean age of 75 years (SD=2). Periodic interviews, biennial administration of questionnaires, and physical examinations every 5 years were conducted to determine biopsychosocial risk variables, age at retirement, and satisfaction with retirement. Results: Early age of retirement was found to be a function of preexisting mental and physical health and later age of retirement a function of occupational status. A surprising finding was that risk factors such as poor objective physical health, low income, and depression, which are commonly associated with poor outcomes in young adulthood and in midlife, were largely unrelated to satisfaction with retirement. Conclusions: A relatively high level of satisfaction with retirement was often attained by men who had reported many risk factors for poor child and midlife development (e.g., low IQ, dropping out of school, poor mental health, and being part of a multiproblem family) but who in later life had some positive resources (e.g., a good marriage, a low level neuroticism, enjoyment of vacations, and a capacity for play). In short, retirement may offer some men a fresh lease on life.