--- - |2 Summary Recent leadership research has drawn greater attention to how the well‐being of leaders influences leadership behaviors, follower performance and well‐being, and overall leadership effectiveness. Yet little attention has been paid to the relationship between occupying leadership positions and job incumbents' well‐being. This research addresses this question by developing and testing a dual‐pathway model. Our model proposes that incumbency in leadership positions is positively related to high levels of both job demands and job control, whereas job demands and job control have offsetting effects on well‐being. Results based on a longitudinal sample revealed that employees who transitioned from nonleadership positions to leadership roles showed trajectories of increasing job demands and job control, whereas such trends were weaker among those who remained in nonleadership positions. Findings from three additional samples generally demonstrated that leadership role occupancy was indirectly related to various indices of psychological and physiological well‐being through job demands and job control. Because the signs of the indirect effects through job demands and job control differed in expected ways, the overall relationship between leadership role occupancy and the well‐being outcomes was generally small and nonsignificant. We discuss research and practical implications of our framework and findings for organizations, employees, and leaders. - Journal of Organizational Behavior, Volume 39, Issue 8, Page 971-989, October 2018.