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This article charts a course from the literature of the classical world through to a select number of classic texts in sociology by Marx, Weber and Bauman, and some more recent psychoanalytically informed studies, to offer a metaphor for the vicissitudes of structure and fluidity in this time of turbulence and extremes. The episode from Homer’s Odyssey featuring the passage of Odysseus and his men between the twin monsters of Scylla and Charybdis is seen as offering an image of the two tendencies of our time towards extreme forms of fluidity in the form of the liberalisation of markets and marketisation of most private and public sectors on the one hand, and a proliferation and mutation of bureaucratic practices seen as an aspect of structural conditions on the other. The dysfunctional relation and polarisation of these tendencies and their consequences are analysed in turn as leading first to a culture of narcissism (Lasch, 1978), then to perversion (Long, 2008; Hoggett, 2010) at a social as well as a socially constructed individual level. The article makes use of free association and amplification in working with images and metaphors.