The study was focused at the factors determining the ability to make reasonable and comprehensive vocational choice by middle school graduates, persuing the goal to develop ways to train this ability. The authors selected the ability to represent a range of possible future outcomes of different choices, considering it to be substantial for making optimal choice. 60 subjects were asked to tell their actual vocational choice and to write about their anticipated future life after this choice. Then they were divided into control and experimental groups equated by age and gender, as well as by volume and depth of their descriptions. The subjects from the experimental group were proposed to work with the interactive computer program LifeLine(r) by A. Kronik, that makes it possible for a user to reconstruct a subjective picture of one's life circle, to reflect on and to correct one's life orientations; after this both groups described images of possible future following 10 variants of vocational choice. Experimental procedure (working with LifeLine(r)) positively influenced qualitative and quantitative parameters of the subjects' descriptions of images of possible future.