I attempt to draw out the existential-spiritual development of T. S. Eliot’s poetic personas from J. Alfred Prufrock to the Fisher King to the Hollow Men to, finally, the “agèd eagle” with “seaward flying / Unbroken wings” of Ash Wednesday. I assess “The Love Song of J. Alfred Prufrock,” The Waste Land, The Hollow Men, and Ash Wednesday with the methodology of Søren Kierkegaard’s brand of existentialism, focusing especially on the individual’s free will in reference to spirituality and religion. I apply Kierkegaard’s theory of the three stages of existence necessary for becoming a true self in interpreting these poems and their progressions. I pay special attention to the themes of existential anxiety (“angst”) and despair in these works, and how retrospectively they productively propel Eliot toward the successively higher stages of existence, and in turn, more developed poetic personas, culminating in Ash Wednesday and even Four Quartets.