People routinely manage the impressions they make on others, attempting to project a favorable self‐image. The bulk of the literature has portrayed people as savvy self‐presenters who typically succeed at conveying a desired impression. When people fail at making a favorable impression, such as when they come across as braggers, regulatory resource depletion is to blame. Recent research, however, has identified antecedents and strategies that foster systematic impression management failures (independently of regulatory resource depletion), suggesting that self‐presenters are far from savvy. In fact, they commonly mismanage their impressions without recognizing it. We review failed perspective taking and narcissism as two prominent antecedents of impression mismanagement. Further, we argue that failed perspective taking, exacerbated by narcissism, contributes to suboptimal impression management strategies, such as hubris, humblebragging, hypocrisy, and backhanded compliments. We conclude by discussing how self‐presenters might overcome some of the common traps of impression mismanagement.