As a form of autobiography, diaries bear witness to the writer’s hermeneutic of the self and offer unique insights into how individuals interpret their experiences on a daily basis. This paper is an analysis of an unpublished 1921 diary of George Grebenstchikoff (1882–1964), a Russian-American writer. I apply a hermeneutic phenomenological lens to provide insights into the writer’s own understanding of his early experiences in exile and the role of language as a tool of cultural immersion as well as a tool of cultural exclusion. The diary holds a special significance for our understanding of Grebenstchikoff’s immigrant trajectory: it documents the gradual transformation his narrative identity, uncovers complex processes of second language learning and first language retention in the context of exile, and demonstrates the author’s historical consciousness. The examination of this and similar texts expands our engagement with the past by bringing us closer to a more nuanced understanding of what it might have been to live in a different era and engages us in the reinterpretation of our own identities.