The purpose of the present study was to examine the relationship between employees’ proactive behaviors in the workplace and their subsequent career satisfaction. In addition to the direct effects, career identity salience and career encouragement were explored as mediators and gender was explored as a moderator. Responses to an online survey from 1,388 employees were analyzed using hierarchical multiple regression modeling. Results showed that there was a strong direct relationship between proactivity and career satisfaction. The addition of career identity salience and career encouragement as mediators in the relationship between proactivity and career satisfaction yielded significant results, while the addition of gender as a moderator in the relationship between proactivity and career encouragement did not produce significant results. It is concluded that career satisfaction is heavily influenced by the amount of encouragement an employee receives at work as well as the degree to which an employee has a balanced work and family life. Explanations and implications of these findings are discussed.