The article examines the impact of digitalization on human life and intellectual experience. The development of computer technology demands an understanding of new aspects of human development and requires a capability to overcome not only external conditions but also ourselves. Entering a new level of development cannot imply a complete rejection of previous dispositions, but should be accompanied by reflection on personal experience and by the quest for new forms of interaction in society and with nature. Communicative and cognitive activity (...) of a person has an ontological basis and relies on processes that actually evolve in nature. Therefore, the creation of new objects is always associated with the properties of natural material and gives rise to new points of support in the development of man. The more audacious his projects, the more important it is to preserve this connection to nature. It is always the human being who turns out to be the initiator who knows how to solve problems. The conformity of complex technical systems to nature is not only a goal but also a value of meaningful construction of development perspectives. The key to the nature orientation of the modern digital world is the human being himself, who keeps all the secrets of the culture of his natural development. Therefore, the proposed by the Russian philosopher V.S. Stepin post-non-classical approach, based on the principle of “human-sizedness,” is an important contribution to contemporary research because it draws attention to the “human – machine” communication, to the relationship between a person and technological systems he created. The article concludes that during digital transformation, a cultural conflict arises: in an effort to solve the problems of the future, a person equips his life with devices that are designed to support him, to expand his functionality, but at the same time, the boundaries of humanity become dissolved and the forms of human activity undergo simplification. Transhumanism engages society in the fight against fears of vulnerability and memory loss and ignores the flexibility and sustainability of natural foundation. (shrink)