This paper argues that the foundation for Skovoroda’s philosophical evolution was laid by the elements of his existential experience: overcoming the fear of death; uncertainty of an individual’s existence in the world; friendship; a series of events in his social life, simultaneous to changes in his works. The most fundamental factor of this experience was Skovoroda’s Christian identity, particularly his continuous efforts to grasp the meaning of the most crucial dogma of Christian religion – the mystery of Resurrection. The totality (...) of these factors caused further development of Skovoroda’s doctrine. The article schematises the inner logic of this development as follows: (1) discovery of the perspective of love, interpreted as being struck by divine beauty; (2) interpretation of human condition as being on the edge of the created and the divine world; (3) proper assessment of the fact that a human being discovers in its own essence the incorruptible beauty of divine image; (4) comprehension of how love to this image arises; (5) interpretation of man as a being that is capable to grasp the eternity of divine charity, and understand itself as a meta-historical entity that has its continuation in eternity. The existential experience brings Skovoroda to a unique and extremely powerful existential experience of the mystery of Cross, which causes a cathartic effect: having undergone the sufferings of the Cross, the material fire of human ἔρως transforms into the living water of divine ἀγάπη, and the confusion of a living creature lost in the world gives way to a tranquil wisdom of a heir of divine gifts and a friend of God. (shrink)