The definitions of success and failure historians use to describe the goals of homesteaders during the late nineteenth century often revolve around arbitrary measures of land and wealth accumulation and persistence. The method allows historians to easily study large populations by dividing them into categories. Doing so reduces complex individuals to a single characteristic – rich, poor, immigrant, native-born, male, female – and removes the agency each person has to create their own definitions of success and failure. Three men – Wesley Hunt, Gunder Olson, and Adam Royhl – of different backgrounds and economic statuses found themselves owning land in the Dakota Territory between 1870 and 1890. Based on past experiences, they brought with them varying ideas of what success meant to them and strategies to realize that success. Studying each individual’s motivations to move, expectations of their new environment, and experiences in that environment allows historians to insert human agency into the process of westward expansion.