In Samuel Beckett’s early novel Watt, a servant’s stay in a manor house becomes the site of a great confrontation with the origins and limits of meaning. Murphy and Watt wearily engage with the Enlightenment rationalism that courses through many of his modernist contemporaries, only to subvert those ideas via processes of philosophical negation. This thesis argues that the novels’ negative, even abject gaze into the heart of anti-foundational truth – that reality is bound by subjectivity, and language is but a hollow vessel – leads to regressive disorder of speech and perception. A theoretical concept of shock, on a continuum with trauma, addresses this duality in the gaze between epistemological damage and the helpless onset of belief. Finally, a close examination of Beckett’s symbolic systems in the novels reveals the true limits of this dialectic well-ahead of its time.