Preconceived notions exist about small-scale farmers in the U.S. Beyond research on new and beginning farmers, few empirical studies have learned directly from small-scale farmers in the U.S. about their perspectives and experiences. By analyzing semi-structured interviews of small-scale farmers in Indiana, this study develops an in-depth understanding of the multi-dimensional motivations and experiences of small-scale farmers and the interconnected, multi-scalar challenges they face. The lack of social infrastructure to support small-scale farmers becomes paramount as they contend with dilemmas of engaging in pluriactivity, securing reliable labor, and navigating relationship building with consumers and peers for both short-term profits and long-term social capital. This study contributes to understanding how small-scale farmers’ motivations, experiences, challenges, and strategies interact to shape their relationship to the land, their farming enterprise, and their perception of and position in the larger agro-ecological-social-economic system, and highlights the need to improve social infrastructure to support small-scale farmers.