The article offers a scientific opinion on the interpretation of event “imprisonment” as a turning point in a person’s life; presents the understanding of the watershed events of life from the perspective of psychological analysis as events requiring a global restructuring of the person and his life-world, as a psychological new growth generated by the system “person” in the present, which determines the shape of the future, thereby restructures the human way of life and the parameters of his life. The description is given to time warp representations of persons sentenced to imprisonment, objectifying themselves in such phenomena as “the narrowing of transspective view of life”, “the violation of the temporal integrity of representations of lifetime”, “the negative past”, “the event of the emptiness in the present”, “the amorphous future”. The understanding of these phenomena allows one to see the violation of the integrity in subjective picture of the life path of the convicted, the weak connections of temporal modes, a tendency to a negative estimation of the events of the past, which in the light of present and future events have lost their meaning, as well as the psychological absence of the present, the indifference to selfstructuring of the personal future.