A conceptual exploration of contrasting psychological phenomena—overconfidence, as exemplified by the Dunning–Kruger Effect (DKE), and self-doubt, represented by impostor syndrome—within organizational contexts. It examines how these biases shape individual behavior, team dynamics, and organizational performance, highlighting the interplay between competence miscalibration and the undervaluation of one’s skills. The article further explores the societal, psychological, and familial origins of these syndromes, proposing implications for leadership and workplace productivity.