Grounded in lifespan development theories that posit a positive influence of aging on emotion regulation, we examine how chronological age and political skill (i.e., a work-related interpersonal competency that functions as an emotion-relevant resource) jointly moderate the relationships between within-person levels of empathy and the use of emotional labor strategies across a workweek. Participants were n = 118 full-time university employees (Mage = 42.85 years; SD = 12.18; range = 20–70), who completed momentary surveys 3 times a day, over a single 5-day workweek. Results show that age and within-person levels of empathy were positively related to momentary levels of deep acting. Considering further the interaction of age, political skill, and empathy, results suggest that the positive relationship between empathy and deep acting is conditional upon age and individual differences in political skill, with differential relationships observed for relatively older versus relatively younger participants. Overall, the findings of this study contribute to a better understanding of the role of age and political skill for daily emotional regulation in the work context.