BACKGROUND Markers of executive functioning, such as prudent planning for the future and impulse control, are related to conscientiousness and may be central to both occupational success and health outcomes. PURPOSE The aim of the study was to examine relations among conscientiousness, career success, and mortality risk across a 65-year period. METHODS Using data derived from 693 male participants in the Terman Life Cycle Study, we examined associations among childhood personality, midlife objective career success, and lifelong mortality risk through 2006. RESULTS Conscientiousness and career success each predicted lower mortality risk (N = 693, relative hazard (rh) = 0.82 [95% confidence interval = 0.74, 0.91] and rh = 0.80 [0.71, 0.91], respectively), with both shared and unique variance. Importantly, childhood personality moderated the success-longevity link; conscientiousness was most relevant for least successful individuals. CONCLUSION Conscientiousness and career success predicted longevity, but not in a straightforward manner. Findings highlight the importance of lifespan processes.