Social media users are routinely counseled to cultivate their online personae with acumen and diligence. But universal prescriptions for impression management may prove for vexing for college students, who confront oft-conflicting codes of normative self-presentation in digital contexts. Against this backdrop, our research sought to examine the online self-presentation activities of emerging adults (18–24) across an expansive social media ecology that included Facebook, Instagram, LinkedIn, Snapchat, and Twitter. Drawing upon in-depth interviews with 28 college-aged youth, we highlight how the imagined surveillance of various social actors steered their self-presentation practices in patterned ways. After exploring three distinct responses to imagined surveillance—including the use of privacy settings, self-monitoring, and pseudonymous accounts (including Finstas, or fake Instagram)—we consider the wider implications of a cultural moment wherein users are socialized to anticipate the incessant monitoring of social institutions—family, educators, and above all, (future) employers.