The present research addresses the dynamic transaction between extrinsic (occupational prestige, income) and intrinsic (job satisfaction) career success and the Five-Factor Model of personality. Participants (N = 731) completed a comprehensive measure of personality and reported their job title, annual income, and job satisfaction; a subset of these participants (n = 302) provided the same information approximately 10 years later. Measured concurrently, emotionally stable and conscientious participants reported higher incomes and job satisfaction. Longitudinal analyses revealed that, among younger participants, higher income at baseline predicted decreases in Neuroticism and baseline Extraversion predicted increases in income across the 10 years. Results suggest that the mutual influence of career success and personality is limited to income and occurs early in the career.