This article attempts to comprehensively examine the phenomenon of individualism at various levels of theory and (family) practice in Russian history in the middle and end of the 19th century through the prism of individualization as the problem. The research resulted in the discovery that approximately at the time when St. John of Kronstadt started writing his diaries as an experience of self-reflection, i.e. form the middle of the 19th century, there appeared and spread in the Russian society the “ego-documents”. The author also shows that St. John was under the influence of St. Petersburg Theological Academy lecturer and psychologist V.N. Karpov, who was one of the students of St. Innocent (Borisov) – the pioneer in his attempts to combine the modern concept of personality and Orthodox dogmatic theology. Also the intellectual tradition of St. Innocent was inherited by Bishop. John (Sokolov) and Archpriest Theodore Sidonskiy. Beyond the framework of St. Innocent “school” the author found similar theological methods of A.M. Bukharev, who placed humanism at the very center of Christianity, and of the Archimandrite Anthony (Amfiteatrov), who described his system of dogmatic theology, responding to the “challenge of modernity” associated with the introduction of the concept of “personality” in scientific and theological discourse. Also, humanism, peculiarly combined with the Christian worldview, is traced in the works of Lev Tolstoy. His ideas intersected with those of the representatives of intelligentsia in the middle of the 19th century, such as A.I. Herzen (social structure), K.D. Cavelin (psychology and law), N.I. Pirogov (pedagogy), who used individualism in different ways in their theoretical (sometimes in practical) constructions. The author also points out the changes in the Russian family that occurred in the middle and end of the 19th century. Those changes affected the transformation of the wedding ceremony, the marriage age and, attitude to women and children, marriage and birth rate, official and actual divorces. The author puts forward the thesis of the relevance of the postulate regarding the almost universal individualization in the Russian Empire in the middle and end of the 19th century, which was manifested in various ways. This study can help clarify the relationship between individualism and the concrete methods of theoretical constructions (art, theology, or any other types of scientific and cultural activities) arising from it and family practices, and thus helps to understand the nature of individualism.