Previous proactivity research has predominantly assumed that proactive personality generates positive environmental changes in the workplace. Grounded in recent research on personality development from a broad interactionist theoretical approach, the present article investigates whether work characteristics, including job demands, job control, social support from supervisors and coworkers, and organizational constraints, change proactive personality over time and, more important, reciprocal relationships between proactive personality and work characteristics. Latent change score analyses based on longitudinal data collected in 3 waves across 3 years show that job demands and job control have positive lagged effects on increases in proactive personality. In addition, proactive personality exerts beneficial lagged effects on increases in job demands, job control, and supervisory support, and on decreases in organizational constraints. Dynamic reciprocal relationships are observed between proactive personality with job demands and job control. The revealed corresponsive change relationships between proactive personality and work characteristics contribute to the proactive personality literature by illuminating more nuanced interplays between the agentic person and work characteristics, and also have important practical implications for organizations and employees.