This paper explores the pitfalls associated with conducting research within a group with higher economic or social status than the researcher. Using examples from fieldwork conducted in Jamaica, I complicate the notion of power in the field by demonstrating that while the raced, gendered, and classed positions of the researcher necessarily affect relations of power in the field; it does not follow that social power or prestige will inhere to the researcher. In the context of differences of race where the researcher is read as disadvantaged or differences of class where the researcher again is read as socially or economically disadvantaged, how is power negotiated? What does it mean to study up? What are the theoretical ramifications of studying up? As more anthropologists choose to study “the privileged” the dilemmas associated with studying up will become more common, particularly for anthropologists of color. The process of studying the production of whitenesses in Jamaica created a rich environment for assessing how my positionality limited access, in some instances increased access, and ultimately changed the parameters of the project itself. This paper examines how the various aspects of my identity affected the work I was able to do in Jamaica.