In urban-influenced areas, farmers face new opportunities and constraints that shape their farming styles. In this article, we investigate the impact of two planning strategies, Ontario’s Greenbelt, Canada, and Toulouse InterSCoT, France, on farmers’ investment and discuss the consistency of farmers’ strategies and territorial projects. A theoretical approach centered on J.R. Commons’ concept of Futurity is operationalized with mental modeling during 41 in-depth interviews with farmers. The results show that farming styles, which reflect farmers’ adaptation to their urban-influenced environment, stem in both jurisdictions from farmers’ values, attitudes, skills, and norms. The differences in investment decisions revealed in the respective planning strategies highlight that Ontario’s Greenbelt zoning is not sufficient to preserve urban-influenced farming, while in Toulouse InterSCoT, the viability of farmers’ projects depends on the alignment of farmers and other agricultural stakeholders’ representations of agriculture. The shared territorial vision of the agricultural landscape stemming from such an alignment may help mitigate potential conflicts while supporting farmers’ projects that contribute to this vision. The importance of a shared vision of the future supporting multifunctional agriculture emerged in both jurisdictions.