The article provides an insight into the interrelation between the worldview and personal meaningful orientations in the context of the modern digital era. The purpose of the article is to investigate the process of generating personal ontology with due regard to personal meaning-making, which involves considering three groups of issues. Firstly, attention is focused on understanding the complexity of the modern epoch against the background of the technological revolution and the effects of virtual imitation of reality, which may determine the (...) worldview. Secondly, an effective insight into life-meaning orientations involves reviewing methodological approaches. Thirdly, the article considers the basic paradigms of life choices including the pragmatic option for self-determination, retrospective reflection based on historical-philosophical inquiry, the paradigm of genetic determination of human behavior and decision-making, and an opposing existential paradigm, which identifies proper life orientations. The study refers to enactivism as a methodological tool, according to which, changes in external circumstances generated by the subject may effect the structure of semantic regulations. The authors come up with an innovative approach to investigating the ways in which the meanings of personal ontology are shaped in the context of complexity and virtualization of the modern world. The idea of the ambivalence of life-purpose relfection is justified. The authors come to a conclusion that structuring personal ontology depends on processing the main tendencies of the epoch in the domain of personal reflection, which is based on one’s inner world and connected with goal-setting and shaping one’s life-project. (shrink)