Ethnography is particularly well-suited to the challenge of debunking the mystification surrounding the cultural production of art. At the same time, ethnographic research itself represents a kind of artistic work, one which not only requires the coordination of multiple social actors working in a collective manner, but also encourages its practitioners to rely on various strategies of impression management and skills of performance themselves. I explore the similarities between ethnography and artistic work by demonstrating the challenges inherent in learning how to conduct ethnographic fieldwork in the context of the contemporary Chicago blues scene. I emphasize three strategies for conducting fieldwork in this context: employing tactics of impression management to establish rapport with informants; participating in a local jam session to develop an understanding of how collaborative circles operate among contemporary blues musicians; and playing blues music in public to subjectively experience how amateurs transition into advanced performers.