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For several years, scientific literature in the field of education and training has highlighted the opportunity to include disciplinary elements within school projects. That is, in addition to knowledge transfer and the training of technical skills. That entails a holistic approach to the individual and to their human and relational development. Hence, the need arises to provide new educational stimuli and instruments, especially for fragile youths, which experience high dropout rates. This paper illustrates the “points-based licence” mechanism, which is an assessment tool devised by CIOFS FP FVG of Trieste—a VET provider. The “licence” system arises from the need to convey students a sense of responsibility for their own actions by monitoring whether they abide by the rules or not, yet without acting exclusively as an impersonal punishment tool. That is, it is effective inasmuch as it works in parallel with well-designed student careers and the push towards self-realization.

Since some time, many authors stated that our Culture has removed emotional and transference dynamics from the educational relationship. For this reason, Pedagogy has to think about pedagogical eros and pedagogical transference as dynamics which always are active in the relationship between educators and students. Therefore, this operation requires a group-training of skills related to the way of thinking and the way in which personal and Community educational actions are thought. Psychoanalysis could give to Pedagogy epistemological and practical insights which are interesting in order to use pedagogical eros and transference. The article aims to understand how pedagogical transference could be used in the educational actions and, on the other hand, it attempts to reflect on what characteristics should have a vocational training aware to pedagogical eros.

E. Morin has been declaring for a long time that radical changes in pedagogical paradigm and educational actions are needed, especially due to the pandemic crisis, which has led to a rediscovery of uncertainty in our life. For this reason, it is necessary to start reflecting on this experience as an educational category, both at an epistemological and existential level. This operation requires the training of skills related to the way of thinking and the way in which personal and Community educational actions are thought, in order to live uncertainty as one of positive and unavoidable human experience. In this regard, it is possible to identify an anthropological harmony between Morin’s insights, phenomenology and psychoanalysis, referred in particular to issues of uncertainty, complexity and “ecology of action”. The article, starting from a field experience in educational and formative ecosystems, aims to define a possible pedagogical anthropology’s proposal, focused to the issues of uncertainty and complexity.