This article is devoted to the investigation of the role, which the systemic reflection plays in the organization, initiation and direction of the process of professional becoming. Reflection is considered as the most important regulative component of personality, which opens to the human the possibility of self-regulation and self-management that allows him to be an active subject of professional becoming. We distinguish three types of reflexive processes, which support the subjective orientation of the process of professionalization and open to the specialists the opportunity to “problematize themselves”. “Problematization of oneself ” on the basis of personal preferences and meanings, which are extracted from the direct experience of prior psychotechnical work, orients the specialists regarding the future steps of professionalization. We discuss the psychotechnical tools, which open the possibility of reflection for working out significant aspects of professionalism. We give self-reports of students who analyzed their professional possibilities by the proposed psychotechnical means.