A good life has long been equated with a happy and satisfied life and a good working life is often thought of as involving high levels of job satisfaction. Job satisfaction, however, is only one aspect of a good working life. Work meaningfulness and work psychological richness are two additional key dimensions of a broader approach to occupational well-being. This study explores how the Big Five personality characteristics and proactive personality are differentially and uniquely associated with the three dimensions of the good working life. In this longitudinal study, N = 612 participants provided data for seven monthly waves. Emotional stability had the strongest positive association with job satisfaction, conscientiousness with work meaningfulness, and proactive personality with work psychological richness.