In this paper, I try to exploit some ideas delivered by Castoriadis and Lasch, in the view of understanding the paradox of the persisting legitimacy of the tenets of Neoliberalism, despite the bankruptcy of its policies. In this respect, the notion of the social imaginary significations seems helpful, shedding light to the predominant self-image of the individual, under Neoliberalism, as entrepreneur of himself. Such self-image isolates the individuals from each other, bolstering their narcissism. As a result, an ideology of individual “autonomy” is produced. As Lasch has pointed out, late Capitalism’s narcissism is the hallmark of heteronomy, immerging individuals in a vain pursuit of power over each other, through the acquisition and accumulation of futile commodities, a pursuit which results to nothingness. The perpetually unaccomplished search for the promised bliss, keeps people attached to this social imaginary signification, not despite, but because of the failure of its promises, in a postmodern version of the myth of the Danaïds sieve.