Manipulating the authority of representational portraiture, I deconstruct historical ideas of secure identity and fixed painting techniques. I highlight contingencies between self and the constructed image as I attempt to clarify my contemporary hopes, fears, and insecurities about racial and socioeconomic progress. By putting myself in the position of sitters from precarious nineteenth- and twentieth-century modes of portrayal, I create work rooted in the need for empathy and a historical desire for connection and feeling. Using multilayered academic painting approaches, I deconstruct the technical and social fabric created by, but not limited to, art-historical traditions. Through a form of self-representation, I emphasize conflicts between the inner and the outer in order to foster new realities and new ways of being understood as not brown or white, wealthy or poor, but human. Often acknowledging the incapacity of classical methods for telling the truth, I stress ideas of vulnerability, false glamorization, and the anxiety of reconciling the past with the present.