Predictions of a fully automated, workless society within two decades have captured public imagination and policy attention. This article examines the empirical evidence and theoretical frameworks surrounding large-scale technological displacement, arguing that rather than eliminating work entirely, AI and automation are more likely to hollow out middle-skill occupations while preserving demand for high-touch human services and augmented knowledge work. Drawing on labor economics, organizational psychology, and technology adoption research, we identify three emerging workforce segments: AI-augmented super-workers, human-essential service providers, and a potentially marginalized middle tier facing structural displacement. The article evaluates organizational responses including skills development programs, hybrid human-AI work design, and social safety net innovations. We conclude that preventing a bifurcated "stipend society" requires proactive intervention in education systems, labor market institutions, and the psychological contract between workers, employers, and the state. The central challenge is not whether society can afford economic security for displaced workers, but whether existing political and cultural frameworks can accommodate such a transformation while preserving human agency and meaning.