The paper will follow the purposes and the literary patterns of the Diary written by V.K. Kiukhel’beker during the years of the imprisonment (1828-1835) and the Siberian exile (1835-1846). The Diary becomes for the poet the unique substitute of the literary and professional milieu from which he was pull up while he considered himself as one of the prominent critics and poets of the young generation. In jail, and later in the Siberian exile, Kiukhel’beker creates an alternative literary world, with internal polemics, discussions, reviews of books and articles, memoirs and perspectives concerning the present and the future of the Russian literature, as if he still took an active part in the cultural life of his Country. Therefore, there are in the writer’s Diary some particularities differentiating it from the general model of diary: at first, the relationship between the author and the diary is something like a mix of typical intimate self-writing and a simulation of public ‘comparison’ (very close to a journal column), where reality and fantasy strictly join and mix with each other; secondly, an interesting peculiarity of this Diary is the predominance of the future tense over the past: Kiukhel’beker is scarcely interested in his own past years, and only partially in his troubled present: he often lives in an ‘eternal’ dimension, writing his Diary for the posterity. Hence, the Diary acquires a didactical or ever prophetical tone, which is typical for Kiukhel’beker’s self-perception.