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This article traces the path of clinical and theoretical reflections developed within a small scientific group of psychoanalysts from the Belgian Psychoanalytical Society (SBP) between 2021 and 2023. The aim is to illustrate the new variety and diversity of clinical situations that psychologists, child psychiatrists, and child and adolescent psychoanalysts are encountering in their consultations today. Indeed, there is a widely shared perception among clinicians of the pre-digital generation that they are no longer confronted with the same demands and clinical presentations as they were twenty or thirty years ago. The hypothesis of this research group is that current societal changes are having an impact on both clinical practice and the psychoanalyst’s countertransference reactions. Psychoanalysts feel challenged and unsettled by contemporary clinical realities, and it has proven valuable to be able to rely on group work to process these paradigm shifts with other colleagues. This process involves co-thinking and co-associativity supported by sharing clinical cases and what these experiences—which are sometimes difficult to bear—evoke in them. This approach allowed participants to discuss complex clinical situations while drawing on the containing structure of the group and shared countertransference dynamics.