This paper reviews literature on employment insecurity and situates objective and subjective employment insecurity in the context of the contemporary economy. I draw on the argument about shifting social contracts to explain both real and perceived pervasive employment insecurity and the frayed American Dream. Employment insecurity derives from the macro-economic changes that produced the social structure of accumulation identified as flexible accumulation that requires employment insecurity as both a form of labor discipline and profit-enhancing strategy. This paper argues that contemporary employment insecurity is both objective and subjective and affects how individuals understand their world and their selves. To this latter point, I look at research on generational differences in the experience of employment insecurity.