Orin M. Jameson, a twenty-one year-old clerk in the 17th Wisconsin Infantry, and James B. Fowler, also a clerk in the 17th Wisconsin Infantry, both kept daily diaries during their time in the Civil War. In their diaries, neither Jameson nor Fowler ever explained their motives for enlisting, nor did they ruminate on the meaning of the Civil War. Their daily diary entries, supplemented with notes in various sections of their diaries, nevertheless provide a unique opportunity to explore how Union soldiers from the same community, who were close friends and related by marriage, who led parallel lives as clerks in the same regiment, used their diaries during the Civil War in ways both very similar and very different. While this article discusses what the Fowler and Jameson diaries reveal about their thoughts, the author of this article is more interested in teaching students to explore how the soldiers used their diaries. This article examines the Fowler and Jameson diaries as a whole to uncover how Fowler and Jameson used their diaries as a tool for processing their experiences during the Civil War and the ways in which their diaries became integral to their experience of the Civil War. This article presents the very practice of diary writing itself as having a profound influence on how diary writing soldiers like Fowler and Jameson experienced and navigated through the war.