This paper focuses on the fluctuations of the Self in two different versions of Modernist poetry as they are proposed by T.S. Eliot and Conrad Aiken. During their stay at Harvard, they read many of the same books and studied the same theories. Both were influenced by William James, Emerson, Bergson, Bradley, the French symbolists, and their instructor Santayana. But the same books and theories generated different modes of comprehension in them. While Eliot offered a condensed vision of philosophy in his works, Aiken tended to depict the long process of self-exploration, which at times resulted in extreme monotony in his longer poetic pieces. Eliot claimed that poetic production supersedes the poet, who functions merely as an agent of its creation; this is quite a contrast with the autobiographical method Aiken applied in his works. Eliot’s name stands for the allusive method in poetry; Aiken’s, for psychoanalytic method. Aiken endeavoured to write a perfect long poem, while Eliot strove for a distilled type of poetry with concrete, economical and exact phrasing. Despite the many differences in form and content in the two versions of Modernist poetry written by Eliot and Aiken, they shared a single vision of life as a journey that sets the personality in a constant flux and presumes a continuous development of consciousness. While Aiken was still influenced by the Neo-Romantics when he depicted the subjectivity of the persona in his early writings, Eliot’s early poetry activated the classicist idea by rendering the objective detachment of his personae.