Ten Nights of Dream was serialized in Asahi Shimbun in 1908, depicting ten stories with strange styles in the form of dreams. It is a unique work written by Natsume Soseki. The plot of “waiting” runs through many stories in Ten Nights of Dream. The first night and the fourth night both depict a waiting story completely, and at the same time they allude to the problems existing in the process of modernization, which finally indicates the return of tradition. Based on the dream theory of Freud’s psychoanalysis, this thesis will center on the first night and the fourth night, seek into the plot of “waiting” in Ten Nights of Dream and its implication, and discuss Natsume Soseki’s views on the process of modernization.