The individual’s quest for enlightenment in Japan is a serious one. One such individual from the medieval Japanese period will be the subject of this paper. Kamo no Chomei, a recluse, poet, and priest who lived from 1155-1216 strove to attain a religious awakening of the mind during the latter half of his life. The question of whether he succeeded or not is a difficult one to answer, however, by examining two of his major works—Hojoki and Hosshinshu—the nature of Chomei’s quest should become clearer. Although I do not believe Chomei found the enlightenment he sought; the quest itself and his expression of it through writing is wholly engrossing. Through my examination of Kamo no Chomei’s writings, the very nature of religious writing will be called into question in conjunction with the role of nonduality. By his inability to separate himself from his hut and artistic expression, Chomei was trapped in dual states and could not achieve the enlightenment of nonduality no matter how hard he tried.