On the basis of historical documents, pedagogical writings of the 19th early 20th centuries and modern works, the paper reveals features of the development of ideas of personality free development in Russian pedagogy in the first third of the 20th century. Their significance for the modern theory and practice of personality-oriented education is assessed. It is determined that by the beginning of the 20th century education had become a strategically important phenomenon, the idea of personality as a value for society was becoming widespread. Schools of pedagogy of individuality were being formed. The content of personality-developing pedagogical systems had been heterogeneous by 19171918, they were influenced by various theories in the context of the relationship between the individual and society. Since the 1920s, pedagogical activity acquired sociocentric contours associated with the upbringing of the socialist type of personality. State educational authorities carefully, but firmly and consistently eliminated religious and other pedagogical influences that did not fit into the established format and ideal of the moral character of a Soviet citizen. At the same time, in socialist education, within certain limits, there was continuity between the ideas of free development and environmental education of the 1920s. The study shows that with unlimited resources in creating a controlled and ideological educational environment, outstanding results can be achieved. However, such results will be ambiguous: blocking personal development, encouraging a programmed influence on a person deprives him of a self-forming beginning, freedom, and ultimately responsibility.