This essay aims to explore modernism's relationship with philosophy by focusing on two novels by Virginia Woolf: To the Lighthouse (1927) and Mrs. Dalloway (1925). It will argue that despite modernism's anti-philosophical stance, Woolf's texts engage with seminal philosophical debates in their own search for truth and invent new ways of re-inscribing literature, the artist, and the arts in the realm of politics. Her novels propose challenging positions to basic philosophical questions associated with the subject/object relationship, the connection between the personal and the political, our shared condition of precarity, or the open-endedness of history. Woolf's modernist/cubist aesthetics and narrative techniques invite new readings of the self and history and anticipate poststructuralist views like those of Judith Butler or Fredrik Jameson.