It is a commonly accepted understanding that the raison d’etre of the five stories comprising A Hero of Our Time by Mikhail Lermontov is to take the readers closer to the protagonist of the novel. In fact, as the narrative progresses, the reader comes to have an increasingly better look at Pechorin, the hero of the novel. This paper aims at unraveling the structural principle of “Pechorin’s Diary,” consisting of “Taman’,” “Princess Mary, and “The Fatalist.” Since the theme of fate runs through “Pechorin’s Diary,” I analyze the use of the keywords “fate,” along with “predestination.” As a result of the examination, it turns out that the protagonist is indeed obsessed with “fate” and his actions can be viewed from the perspective of his ambivalent interpretation of fate. More importantly, the three stories of “Pechorin’s Diary” reveal the tendency of attributing Pechorin with the sense of omniscience and omnipotence. While Pechorin is described to be lucky in averting a life-threatening scheme against him in “Taman’,” he assumes a role of both agent and victim of fate in his plots against Grushnitsky and Mary in the next story. Pechorin’s image with regard to fate reaches its climax in the final story “The Fatalist,” in which he not only reads someone else’s predestination, but authors it for himself. This final stage of the protagonist’s self-fashioning image reminds the reader of Lermontov’s another masterpiece The Demon.