This thesis studies on the psychological and aesthetic corresponding progress concerned with the life of the colonial society through the research of the Lee-sang's novel into form.. The prototypical form of the Lee-sang's literature originates from the sense of the ambivalence that is formed by the experience of the colonial modernity. Lee-sang's sense of the ambivalence develops into a paradox from his first work 『the 12th on December』 to 『Wing』 and 『Dong Hae』.The paradox -an aesthetic form- weaves out the narrative of the repeatition impulse through which Lee-sang is trying to pursue the original object of desire and fails in it at last.. The end of the narrative led by the repetition impulse is always the time and place of the despair that the original object of the desire is damaged. Lee-sang's novel, however, rises in quality at the climax of the despair and exposes the truth that a society hides through the power of the paradox. Therefore the outcome of this thesis is to investigate the principle and process producing an aesthetic structure by which a writer's specific psychological phenomenon penetrates into the substance of the real society.