The present research uses an economically diverse, middle-aged sample to examine the concurrent and longitudinal interplay between personality and occupational experiences. Using the Five-Factor Model of personality and the Demand-Control Model of the occupational environment as guiding frameworks, participants (N=722) reported on their personality, job characteristics, and occupational history; a subset (n=297) made the same ratings approximately 10 years later. Measured concurrently, emotionally stable, extraverted, open, and conscientious participants reported jobs with greater decision-making latitude, whereas disagreeable participants had more physically demanding and dangerous jobs. Longitudinal cross-lagged analyses revealed that personality was associated with changes in decision latitude, hazardous working conditions, and physical demands. None of the job characteristics predicted change in personality at the factor level. Thus, personality shaped occupational experiences, but occupational experiences had minimal impact on personality. Support for the Five-Factor Theory perspective and implications for environmental approaches to personality development are discussed.