The purpose of this study is to link Eliot’s exploration of “silence” and “negation” in Four Quartets with Derridean deconstruction, especially his essay, “How to Avoid Speaking.” The Eliot/Derrida parallel of this paper deals with a real question that one work can illuminate the other, rather than pursuing the similarities of their thoughts and revealing the interactions or influences. Eliot and Derrida share a common distrust of language. Eliot’s exploration of the void seems to be close to Derrida’s assertion, and Eliot’s “still point” is like an approach to the idea of différance. Throughout his career, the sense of the void never really leaves Eliot. Derrida also mentions about his implicit relation to negative theology. In Four Quartets, however, we can locate his turn toward the value of humility as an important difference between Eliot and Derrida. Eliot raises a question whether silence, in surpassing language, indeed fulfills the vision of unity and eternity; or only by negation can we indicate what remains forever beyond the conditions of representation. Thus one of his greatest concerns is the spiritual vicissitudes of finding and keeping a viable way.