In order to better understand how people work in the Web-enabled workplace, we examined the phenomenon of personal Web usage (PWU). We analyzed 316 responses from those with Web access at work to the question, “Do you think it’s ok for a person to use the Web for non-work purposes during working hours in the workplace.” The responses were coded into 19 themes and four categories. Using correspondence analysis, concept maps were generated which revealed that personal Web usage in the workplace is a complex issue with not only a potentially dysfunctional dimension, but also a potentially constructive one. Organizational position was an important variable with top, middle, lower-level managers, as well as professionals, and administrators positioning in different spaces on the conceptual map. Further analysis using Q-methodology reinforced the dual nature of PWU and the importance of position. Drawing on our results, an extension of the social contract theory and a model of personal Web usage in the workplace were suggested.