Does psychopathy have an upside in vocational contexts? Applying the triarchic model of psychopathy, we propose that the dimensions of boldness, disinhibition, and meanness have different relations to workplace outcomes. Focusing on boldness and in line with socioanalytic personality theory, we propose that political skill moderates the relation between boldness and job performance. Using a sample of 477 target-coworker pairings, we found interaction effects of boldness and political skill on contextual and task performance, and the buffering of counterproductive work behavior. Furthermore, political skill moderated the relation between boldness and adaptive performance. Disinhibition and meanness were positively correlated with counterproductive work behaviors, thereby reflecting the dark core of psychopathy. In sum, boldness is a trait linked to career success in the absence of the other traits that make up psychopathy as a whole. Furthermore, we encourage the use of the triarchic model as an overarching framework in vocational contexts.