Recognizing the inherent pressures on farm families and farmland, USDA has been developing policies and programs that simultaneously attempt to retain existing farm families on the landscape, recruit new farmers, and create lasting economic opportunities rooted in agriculture. In this article we argue that to date there has been an overemphasis on economic and structural approaches and a systematic discounting of the way individual farmer and farm household motivations can differ as they relate to the farm household life cycle, enterprise growth, adaptation, and reproduction. We use a sociological lens to qualitatively and quantitatively examine the social differences between multigeneration and first-generation farmers at the rural-urban interface by exploring how economic and noneconomic values influence succession plans and enterprise structure. We find that the answers to these questions are complex, layered, and not static, as farm households cycle through the life course. We describe how the differences between young and old multigeneration and first-generation farmers can influence the structure of agriculture at the rural-urban interface, and conclude with some practical policy recommendations.