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The article reconstructs individual characteristics of the subjects of the initial colonization of Siberia and the Far East and episodes of their advance to new lands. The main methodological approach of the research is the principle of historicism, as well as the principle of “activity constitutes”, widespread in psychological science, according to which identical activities and external conditions should give rise to similar worldview systems. On the basis of this premise, the possibility of judgments by analogy is substantiated in relation to the motives and goals of the first colonizers of Siberia based on the materials of the development of the Far East by the Russians. On the basis of materials of personal origin, the author examines the strategies of legitimizing individual actions of the pioneers through forcing the factor of external threat, as well as using the idea of “state good”. The colonialists use these arguments as a justification for their own actions in the east. At the same time, the acts of colonization undertaken by them have an adventurous connotation characterized by actions with a pronounced emotional component of the decisions made. The problems of relations with aborigines are considered separately. It is concluded that the idea of “peaceful peasant colonization”, which has a civilizing significance for the local population is untenable, as well as the conventionality of the transition of the aborigines under the authority of the Moscow government, which is fully realized by the pioneers.