Previous research has been inconsistent in the prediction and empirical findings regarding work–family enrichment and satisfaction. The current research seeks to clarify this inconsistency by examining both directions of work–family enrichment (work-to-family enrichment and family-to-work enrichment) with both job satisfaction and family satisfaction to determine if their effects are similar or diverse. Building on the theoretical foundation of Fredrickson’s broaden-and-build theory, the authors explore the mediating roles of psychological distress and positive mood in this process. Using a sample of 310 working respondents, the authors found that psychological distress was a mediator to both job satisfaction and family satisfaction, while positive mood was a mediator to job satisfaction but not family satisfaction. Further, the authors found that the direct effect of work-to-family enrichment was on job satisfaction, the originating domain. In addition, the total effect of enrichment to satisfaction (through the mediation mechanisms of distress and mood) was again in the pattern of the originating domain such that work-to-family enrichment more strongly influenced job satisfaction. However, family-to-work enrichment did not directly impact family satisfaction, nor was it significantly stronger than work-to-family in its total effect on family satisfaction.