This thesis investigates the contemporary art market in relation to the practices of working artists. The social mechanisms that determine artistic value influence the decisions and processes of all artists. Simultaneously, the economic structure of the art world is complex and perhaps challenging to navigate for those who are engaged in a creative practice. As a critique of the current economic systems that govern the art industry, two key questions are addressed through this research: How are financial and symbolic values attributed to art? How do profit-driven art institutions affect cultural production? Issues of artists’ rights, representation, and the feasibility of a career in the arts are also examined. By looking at commercially-oriented institutions such as auction companies in juxtaposition to the knowledge-based institutions of art scholarship, this thesis considers the theoretical and discursive logics at play in artists’ financial decision making and suggests options for combining aesthetics with entrepreneurialism.