This chapter examines Virginia Woolf's “contradictory thinking” and argues that her thought is resolutely “dialectical.” It begins by discussing some of the modalities of the presence of contradiction in Woolf's thinking about being, history, art and even thinking itself in their various inter-articulations and ethico-political implications. It then cites a number of Woolf's essays including “How it Strikes a Contemporary” (1923) and “On Not Knowing Greek” (1925) to demonstrate how Woolf works through oppositions between the classics and the moderns, the present and the past, continuity and change. It suggests that even though Woolf politically contests historical contradictions which point to and sustain various forms of oppression, she equally employs contradiction as a means of thinking about a subject, especially in her essays. It also considers how Woolf seems to line up with the Marxian tradition of dialectical materialism which recognizes in identifying contradictions a political task, a revolutionary chance against a history of oppression.