Abstract: | While prior research has identified several individual characteristics and contextual factors influential on an employee’s quantity of self-development participation, no research has examined multiplicative effects among these factors. This study investigated person-situation interactions among five individual characteristics (e.g., openness to experience) and the contextual factor of workplace support for self-development. This study also sought to investigate the link between proactive personality and self-development participation, a promising individual characteristic that has received little attention in the self-development literature. Data collected from 136 employees demonstrates significant interactions between workplace support with learning goal orientation, openness to experience, and conscientiousness. As hypothesized, workplace support is more strongly, positively linked to quantity of self-development participation for employees lower in these traits. In contrast, the provision of external support is rather inconsequential for those high in these traits, as these employees demonstrate an internal propensity to engage in voluntary development regardless of the support available. Regarding proactive personality, a significant positive relationship was observed with self-development quantity. Further, although the expected interaction between proactive personality and workplace support did not reach statistical significance (p = .056), it was in the hypothesized direction. |