The vast majority of research on self-monitoring in the workplace focuses on the benefits that accrue to chameleon-like high self-monitors (relative to true-to-themselves low self-monitors). In this study, we depart from the mainstream by focusing on a potential liability of being a high self-monitor: high levels of experienced role conflict. We hypothesize that high self-monitors tend to choose work situations that, although consistent with the expression of their characteristic personality, inherently involve greater role conflict (i.e. competing role expectations from different role senders). Data collected from a 116-member high-tech firm showed support for this mediation hypothesis: relative to low self-monitors, high self-monitors tended to experience greater role conflict in work organizations because high self-monitors were more likely to occupy boundary spanning positions. To help draw a more realistic and balanced portrait of self-monitoring in the workplace, we call for more theoretically grounded research on the price chameleons pay.