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The paper is a reflection on the conflictual relationship between adaptation and subjectivity, persona and individuation, starting from Jung’s seminal writings, and their developing features in contemporary society. With reference to sociologist Zygmunt Bauman’s speculations on so called liquid society and retrotopia, concepts like nostalgia are examined in the article. A case of a manic and violent nine-year-old child, a millennial-to-be boy treated in the mid-nineties, is presented to describe issues like shame, object promiscuity, consumerism and overexcitement, and suggests questions on whether and how these patterns would be different for patients belonging to the Generations Z (born between 1996 and 2010) and Alpha (born after 2010). The case material shows how the construction of a suitable persona was the only aim of the child’s family, in terms of a merely quantitative regulation, their model being that of being adequately capable of consuming and being consumed, using each other for utilitarian purposes, and essentially avoiding the sense of self-and-other as live objects. Psychoanalysis is theoretically and clinically challenged and confronted with the conflict between the new features of adaptation and a dimension of subjectivity whose traits are more and more difficult to detect.