Anxiety prevails when the faith in life is absent. It is the uncertainty that causes anxiety. Uncertainty as a source of anxiety consists of several conceptual elements, which are, to name a few, existential uncertainty, cognitive uncertainty, moral uncertainty, and aesthetic uncertainty. The social uncertainty indirectly related to aforementioned uncertainties, however, is directly related to the prevailing dilemma of “not knowing how to live on” and is the very source of collective anxiety. This article seeks to address the following agendas: 1) examine the social anxiety as a source of collective anxiety with emphasis on flexibilization thesis; 2) describe the unique characteristics embedded in South Korean society where collective anxiety is being aggravated; 3) explore the directions and strategies for possible countermeasures.