To advance understanding of career wisdom’s role and broaden empirical support for the dual-process theory of career decision-making and adaptation (DTC), the present study investigated the reciprocal relationship between career wisdom and proactive career behavior. Using a sample of U.S. workers (n = 995), it tested a cross-lagged model of these variables across three time points. From Time 1 to Time 2, career wisdom positively predicted subsequent proactive career behavior while controlling for baseline proactive career behavior, and proactive career behavior positively predicted subsequent career wisdom while controlling for baseline career wisdom. From Time 2 to Time 3, career wisdom did not predict subsequent proactive career behavior when controlling for baseline proactive career behavior; however, proactive career behavior continued to positively predict subsequent career wisdom while controlling for baseline career wisdom. These findings offer important evidence in support of the DTC, underscoring the reciprocal benefits of career wisdom and proactive career behavior as well as the importance of their dialectical management. Limitations and directions for future research are also discussed.