The present study examines relationships among differences in personality, financial planning behaviors, and retirement life satisfaction. The hypothesized sequence of relationships is: PersonalityàFinancial Planning BehavioràRetirement Life Satisfaction. The study adds to prior research by clarifying the hypothesized role that proactive personality (as opposed to other personality variables such as the Big Five) has as a predictor, and also by showing how differences in discrete types of financial planning behavior influence retirement life satisfaction and mediate effects of proactive personality on satisfaction. This study tests these linkages while also addressing limitations and ambiguity in prior research regarding these potentially important effects among disposition, financial planning and a satisfactory retirement.