In the context of the institutional transformation of education and the complication of the processes of its functioning and development in the information age, the problem of analyzing the self-assessment of educational success as a subjective regulator of human educational activity becomes of particular importance. The article examines the subjective assessment of success in formal education as a reflection of students' ideas about the degree of compliance with the system of institutional requirements through their acceptance / rejection. The analysis of the problems of educational success is bazed on the material of a large-scale sociological study of schoolchildren, students of secondary vocational education (SVE) and universities of the Sverdlovsk region (N = 2489 people). There were carried out the typologization of subjects of educational activity in accordance with the level of self-assessment of educational success; comparison of the types identified during the transition from one subsystem of education to another (school - secondary vocational education - university); determination of individual-personal and institutional contradictions and conflicts in the assessment of educational success as points of growth, the search for coordination of the needs and interests of the individual, on the one hand, and education as a social institution, on the other. The author comes to the conclusion that the self-assessment of educational success is a stable institutional construct that uniformly regulates educational activity at all stages of education, carrying out the process of differentiation of its subjects. At the same time, it can be dysfunctional in relation to the institution of education, its implementation of an adaptive, socio-cultural function, the function of professional self-determination. The results of the sociological study demonstrated that the institutionally formed model of self-assessment of success for educational communities in the current conditions is not optimal. Gradually transforming in accordance with the needs of students, the possibilities of the educational institution, the challenges of the time, it will have to change, creating conditions for broader prospects and diversity of the educational and professional future of students.