As an emerging Chinese indigenous leadership style, paradoxical leadership has received considerable attention from researchers. Many studies have demonstrated the positive impact of paradoxical leadership on employees, teams, and organizations; however, there is less information on how paradoxical leaders influence their own work outcomes. On the basis of self-regulation theory, in this study, we examined the impact of paradoxical leadership on leaders’ task performance. In addition, we investigated the mediating effects of job crafting and career resilience on this relationship. Through a survey of 120 leaders and 271 of their immediate followers, our empirical analysis found the following: (1) paradoxical leadership was positively related to leaders’ task performance, (2) job crafting mediated the relationship between paradoxical leadership and leaders’ task performance, and (3) career resilience positively moderated the relationship between paradoxical leadership and job crafting, and had an indirect effect on task performance through job crafting. Our model offers novel insights into the paradoxical leadership literature and implications for improving leaders’ job crafting and task performance.