This paper is devoted to the analysis of the notion of solidarity in Sergius Hessen's philosophy. He applies macrosociology of the Southwest School of Neo-Kantianism to determine the principles of interaction between an individual and a culture. The axiological method allows one to understand reality as the opposition of value and fact. A culture is a process of improving the realization of values. According to Hessen, values exist independently of any individual. In this case, any person is free, he or she is not a mechanism for the formation of culture. Freedom is a necessary condition for the creativity of an individual, which makes it possible to contribute to the development of this culture. However, there is no unambiguous interpretation of freedom. Freedom is a value, like science and art, so its content is revealed in different ways in different cultures. Any individual realizes his or her freedom in creativity. But creativity is possible only as making a personal contribution to the embodiment of a cultural value. According to Hessen, a person can understand the logic of embodying a value in a certain culture due to Hegel's dialectic. The dialectical method is a scheme for understanding the dynamics of the embodiment of cultural values. Thus, through the dialectical method, every person can understand the specifics of the development of culture and determine the directions for self-actualization. Solidarity allows each individual to assess the current system of communities and institutions of a certain culture, and determine what needs to be changed to achieve personal freedom. Solidarity creates the possibility of correlating the tasks of cultural development and individual freedom ensuring. A common will is formed in society; this will determines whether the current system of communities and institutions corresponds to the potential for realizing personal freedom. Solidarity allows us to evaluate cultures in terms of tolerance as equivalent phenomena, each of which has its own specificity of freedom development. Therefore, the interpretation of the freedom of one culture is not suitable for determining freedom in another culture. Summing up, this paper proves that it is possible to determine the degree of freedom in a particular society only as a result of an analysis of the obstacles to personal creativity in the context of the system of communities and institutions in a certain culture.