Audiences generally view people who display more (versus less) comparative optimism more favorably. We explored whether audiences view a target who displays comparative optimism as more professionally successful and conversely, whether they view a target who is more professionally successful as more comparatively optimistic. In Study 1, participants estimated the career success of a target that varied in level of comparative optimism. In Study 2, participants estimated the level of comparative optimism of a target that varied in career success. The results revealed that observers rated comparative optimists as likely to have successful careers, and rated people with successful careers as likely to display comparative optimism. Inferences about personal agency account for the bidirectional relationship.