Harry Frankfurt has argued that what matters most deeply is not whether everyone has the same resources, but whether each has enough. Under either criterion, however, law professors should be doing extraordinarily well. We have job security, financial security, freedom and prestige—in amounts that far surpass most dreams. We should therefore experience consistently high levels of job satisfaction. Nevertheless, large pockets of the legal academy exhibit a surprising level of dissatisfaction—which undermines both fulfillment and productivity. This dissatisfaction can come out in, for example, overly general patterns of criticism; and in our patterns of attention, which are sometimes drawn away from what we might contribute to a given situation and toward a more anxious evaluation of self and others. It can be fueled by perceptions of undercompensation (by wealth or prestige), by the growing role of SSRN and citation rankings, and the like. This raises important questions: What are the sources of this dissatisfaction? Are they real, or might they arise from culturally-ingrained conceptions of our roles in the academy, and how we add value? How might these conceptions shape our professional interactions, and thereby affect the way our ideas and profession develop? Finally, what are our options?