The Provincial Health Services Authority (PHSA) of British Columbia suggested that a paradigm shift from weight to well-being could address the unintended consequences of focusing on obesity and improve the outcomes of efforts to address the challenges facing both individuals and our healthcare system. In this paper, we jointly used artificial intelligence (AI) and participatory modeling to examine the possible consequences of this paradigm shift. Specifically, we created a conceptual map with 19 experts to understand how obesity and physical and mental well-being connect to each other and other factors. Three analyses were performed. First, we analyzed the factors that directly connect to obesity and well-being, both in terms of causes and consequences. Second, we created a reduced version of the map and examined the connections between categories of factors (e.g., food production, and physiology). Third, we explored the themes in the interviews when discussing either well-being or obesity. Our results show that obesity was viewed from a medical perspective as a problem, whereas well-being led to broad and diverse solution-oriented themes. In particular, we found that taking a well-being perspective can be more comprehensive without losing the relevance of the physiological aspects that an obesity-centric perspective focuses on.