The article explores the concepts of individualism and collectivism through the lens of fundamental transformations occurring within the individual as a subject of social action. The author introduces an original framework conceptualizing social action as a dichotomous unity of freedom and algorithm, or free and algorithmized action. Within this paradigm, the subject of social action is understood as a synthesis of actor (acting subject) and agent (subject-function). The unfolding and resolution of this contradiction manifest differently in Western and Russian contexts, which are analyzed as two distinct versions of modernity, differentiated by the degree of market relation development. It is demonstrated that technological development within market conditions engenders a technological system that colonizes society holistically, including its cultural sphere. Free action is replaced by algorithmized action, leading to the displacement of the actor by the subject-function. Consequently, the individual is reduced to a functional element of the technological system, transformed into an atomized unit capable of equally executing programs of individualism or collectivism. In contrast, Russian (Soviet) modernity, characterized by a limited market, exhibits a reverse colonization, or symbiosis, between culture and system, which preserves a space for free action and the actor. Under these circumstances, the dialectic of individualism and collectivism becomes a nuanced process, potentially encompassing individualists oriented toward the common good. Collectivist orientations emphasize alignment with a “good collective” and the value of friendship. Contemporary trends are marked by contradictions, as the expansion of the technological system coexists with the persistence of individualism and collectivism rooted in Russian (Soviet) modernity. The article concludes by suggesting that the Russian experience of modernization offers valuable insights into achieving a balance between individualism and collectivism, algorithm and freedom, technological development and the preservation of human individuality under current conditions of global transformations.