The article studies educational trajectories of teachers, psychologists and school principals. Their subjective semantics or systems of meaning – viewed through the narratives on the respondents’ activities – were examined with a specially designed semantic differential called “The Educational Trajectory”. The analysis showed that teachers associated the results of their educational work, primarily, with its content estimated with the qualities like “competent” and “strategic”; and secondarily, with the qualities like “dynamic”, “representative”, “personal” and “conventional”. School psychologists implied that their educational trajectories were more about comfort and less about consistence, meaningfulness, representativity and correspondence to expectations or reality. School principals’ semantic model of educational trajectory was more cognitively complex and balanced compared to the ones of teachers and/or psychologists. School principals’ semantics concerning educational activities were characterized by a deliberate cognition, and, additionally, by usefulness, meaningful content, comfort, personification, continuity and competency. The study highlights the development of the latter in the terms of so called “emotional remnant” of educational activities. The authors have proposed a set of major principles/conditions to design individual educational trajectories. First, it is predetermined subjective semantic content that facilitates constructing certain individual educational trajectories. Second, it is the genesis of the content of educational trajectories unfolded on the following dimensions: cognitive complexity, diversification, stereotype educational activities. Third, it is a mixed composition of developers participated in different projects aimed to foster individual educational trajectories which promotes a shared meaning space and enriches it with unique individual trajectories of different school personnel via a synergetic self-organization mechanisms.