The paradox of proactivity suggests that a proactive personality might be destructive for employees and organizations. However, the boundary conditions that allow proactivity to result in positive outcomes remain unclear. In line with proactivity research and emotional dissonance theory, the authors investigate whether and how a proactive personality influences employees’ emotional labor strategies, job performance, and career satisfaction. They also note the potential moderating role of perspective taking, along with the benefits of perspective taking on perspective takers. A three-wave study involving 145 frontline employees and their immediate supervisors in the Chinese hospitality industry tests the research model and reveals that employees’ deep acting mediates the interactive effects of a proactive personality and perspective taking on job performance and career satisfaction. In addition, surface acting mediates the influence of this interaction on career satisfaction but not job performance. These findings have theoretical and managerial implications for proactivity, perspective taking, and emotional labor theory and practice.