The present research focuses on the role of disgust, shame and guilt in the identity formation of Stephen Dedalus in A Portrait of the Artist as a Young Man and Gabriel Conroy in “The Dead” by James Joyce. In both, there is a quest for an independent, and authentic identity through gradual emancipation from the nets of family, religion, nationality, culture, and language and embracing life in total liberation, however, through different paths, leading into different destinations. While Stephen decides to leave the country and pursue his goals somewhere else, Gabriel stays at home and tries to follow a more liberal customized life in his territory. Benefiting Martha Nussbaum’s ideas in Hiding from Humanity, the current study explores the role of shame and guilt, as the controlling tools, in breaking individual’s defense mechanism and selfreliance by imposing the sense of inadequacy and inefficiency to make his/her mind malleable and flexible enough to absorb the desired values and standards. The present research reveals the equivocal and ambivalent nature of those nets, as both supporting and restricting. To find one’s voice and authenticity, the individual must liberate him/herself, fly over the labyrinthine maze of culture and tradition, and embrace self-alienation as an opportunity for self-realization. The ready-made identities the society gives, have not the capacity for a liberal life, where the individual actualizes his/her non-transferable and unique potentialities and talents. What the nets do, is normalizing the society to be a unified homogenous body at the cost of killing the very liberal and humanist soul of self-awakening.