This article concerns the way the Federal army servicemen viewed their antebellum and postwar career. The research is based on diaries and letters of the Union officers and men coming from diverse social backgrounds and geographical regions of the Nineteenth Century USA. Union Army officers' and privates' attitude towards their antebellum economic activity is not formed solely by nostalgia and is in many ways critical. At the same time, their evaluation of the war's influence on their future postwar career is, with some exceptions, overwhelmingly negative. Nevertheless, Union army service members cannot be esteemed as lost and panicked in the face of their postwar future. For instance, self-sufficient married farmers were expecting to get back to their prewar labor of being farm owners and heads of their families. Many soldiers and officers of young age from both rural and urban areas came to general understanding of what trade or other type of economic activity they want to choose. Moreover, some of them had already found a specific employer or their own enterprise before the conflict ended. It is important to admit that not all of them based their career plans on pure economic rationality – for many of them such factors as proximity to their relatives or fulfillment of their individual promise were more vital than level of income. Another significant part of the source material used in this article presents the situation of choice between several career options.