In modern work environments characterized by change and uncertainty, work adjustment, consisting of adaptive and proactive behaviors, is identified as an important activity in achieving and/or maintaining person-environment (P-E) fit. Derived from the theory of work adjustment, we propose that work styles fit generates a boundary condition for the successful implementation of adjustment behaviors. With respect to enacting work behavior, work styles fit describes the level of correspondence between an individual's activity and effort as applied over time with that suited to the environment. Two 2-wave hierarchical moderated regression analyses were conducted examining the effect of job change negotiation behaviors and career initiative behaviors upon demands-abilities (D-A) fit. Results demonstrate that adjustment behaviors contributed to an increase in D-A fit across time, but only in the context of high work styles fit. When work styles fit was low, engaging in adjustment behaviors resulted in a decrease of D-A fit. The theoretical and practical implications, as well as proposals for future research regarding dynamic conceptions of P-E fit, work styles fit and proactive behaviors are discussed.