The article traces parallels between some confessional situations in the poetry of Vyacheslav Ivanov and the Confessions of St. Augustine. The question is raised about the ability of Ivanov`s symbolism to reproduce the existential uncertainty (ignorance of the further path, the actual rejection of its foreshadowing by culture and intellectual experience), to which the confession should lead the subject, if s/he follows the principle of Augustine`s „transcende te ipsum”. When the state of confession is pre-established by a system of symbols with a „ready” meaning, it risks losing its uniqueness: the confession can be replaced by some universal „scheme” of confessionality, which happens in a number of the Ivanov`s poems. Thus, the article delineates one of the possible perspectives of the further study of the claimed topic.