The article examines the problem of “contradiction” in the text of Prince (knyaz) Vladimir Monomakh’s “Instruction”. The researcher encounters a foreign consciousness that is closed off “to us,” yet at the same time is as “open” as possible to contemporaries, due to the fact that the key meanings are linked by a communicative connection between the writer and the Old Russian reader. The problem of the contradictory nature of the “Instruction,” which has long attracted the attention of researchers, lies in the discrepancy between Monomakh’s ethical principles and their “practical implementation”. The author’s statements require “expanding” the text to a context in which a certain general “rule” may become clear. Based on an analysis of the author’s direct statements, the teleological foundation of the work is established. To understand the cultural background of the “Instruction”, the reconstruction of conventional models is carried out.