Informed by evolutionary leadership theory, the current study investigates two forms of leader well‐being in the workplace as explained by leaders’ self‐perceived identity (i.e., self‐ratings of dark personality), follower‐judged reputation (i.e., subordinate‐ratings of leaders’ dark personality), and attributed charisma. Results, based on data from 386 followers matched with 268 leaders, linked both a Dark Triad identity and a Dark Triad reputation to less perceived social worth and job satisfaction among leaders. Additional results found leader charisma surpassed a Dark Triad identity and reputation as an explanatory factor, a finding we attribute to the salience and observability of charisma to followers. Lastly, our results also indicate a leader identity × charisma interaction. The pattern of moderation suggests followers respond to leader charisma in ways that encourage a leader and thereby buffer the otherwise inimical consequences of a Dark Triad identity. Overall, our research suggests that leaders’ subjective quality of work life is shaped by an interplay between internal propensity and acclaim from followers in the form of attributed charisma. Implications for organizations and evolutionary leadership theory are discussed.