This research examines how people manage online personal brands in a Web 2.0 context. Using a novel mixed-method approach and consenting participants, the authors generated digital brand audits of 12 people and asked undergraduate students and a human resources professional to judge their profiles (made anonymous), both qualitatively and quantitatively. After comparing these evaluations with participants’ own judgments of their online profiles, the authors conducted long interviews to understand how people manage online profiles and feel about others’ judgment of the content they post. According to these results, people engage in personal branding, though their efforts are often misdirected or insufficient. They consider personal online branding challenging, especially, during life changes or when managing multiple audiences.