Abstract This theoretical study investigates contemporary experiences of alienation through five major societal transitions: individualization, performance pressure, technological overload, loss of meaning, and ecological awareness. Drawing on key psychoanalytic concepts, particularly the role of the Other in the constitution of the subject, we systematically analyzed primary works by Freud and Lacan alongside interdisciplinary secondary literature. This analysis followed an iterative thematic approach, through which recurring patterns, conceptual tensions, and shared problem framings across these bodies of literature were identified and synthesized into the five overarching societal transitions. Our findings suggest that modern freedom often coincides with intensified inner deficiency, shifting the locus of control from external authority to internal demands and self-exploitation. The digitalization of daily life, the performance-oriented ethos, and the erosion of boundaries between public and private spheres generate new forms of discomfort. Simultaneously, heightened climate awareness resulting from unsustainable economic growth produces both hope and collective anxiety or guilt. Empirical research supports this psychoanalytic reading, with increasing signs of burnout, loneliness, and climate-related distress. The article concludes that psychoanalysis not only clarifies these phenomena but also offers a critical perspective on the paradoxical demands of modern culture. Recognizing alienation as a structural element of human existence, which is amplified via contemporary socioeconomical circumstances, opens space for renewed dialogue and reconsideration about our relationship to work, technology, others, and society.