Educators perceive the phenomenon of "educational pathway" as a system characterized by strength, comfort, ability to be represented, dynamism, personalization, and innovation. The author presents the results of a study into the variability of educators’ assessments of and attitudes towards their own educational pathways, which was carried out using a specialized semantic differential “Educational pathway ” and cluster analysis of integral variables. It was found that the respondents assessed their educational pathways as deficient (13.5%), transitional or hybrid (57.6%), and surplus (28.9%), while the educators’ educational pathways were divided into six types. The first type of the assessment of and attitudes towards the educational pathway (13.5%) was described as deficient, while the educators of this type were called "educational nihilists". The second type (4.2%) was called transitional because, on the one hand, it lacked comfort, innovation, dynamics, and systemic vision of the educational pathway, and on the other, it had resources of the regulatory and conscious component and personalization; the representatives of this type were called "dissatisfied performers». The third type (11.3%) was transitional with a marked tendency to surplus along with a domination of negative parameters of continuity and system; the educators of this type were called "productive chaos-makers". The fourth type (17.9%) was transitional with mostly positive attitudes and rich innovation and personalization resources; the educators of this type were called "satisfied routine workers". The fifth type (24.3%) was deficient in terms of the integrated systemic vision of the educational pathway and the absence of a full and strategic "picture" of the educational pathway along with positive assessments of other structural components; the educators of this type were "successful tacticians" of their educational pathway. The sixth type of the educational pathway assessment (28.9%), which was surplus, was characterized by educators’ satisfaction with their educational pathways, their effectiveness, emotional comfort, convenience, simplicity, dynamism, novelty and personalization; the educators of this type were called "absolute positivists." The presented typology is of interest not only because of the variety of assessments of and attitude towards the personal educational pathway, but also because of the possibilities for finding out the functionality of each type for realizing educators’ personal potentials, studying the transformation rationale and designing educators’ educational pathways theoretically and empirically.