Sustainability has emerged as a concern of central relevance. As a wicked problem, it poses challenges to business-as-usual in many areas, including that of modeling. This article addresses a question at the intersection of model-driven engineering and sustainability research: ‘How can we better support sustainability by bringing together model-driven engineering, data, visualization and self-adaptive systems, to facilitate engagement, exploration, and understanding of the effects that individual and organizational choices have on sustainability?’ We explore this question via an idealized vision of an evaluation environment that facilitates integration and mapping of models from multiple diverse sources, visual exploration, and evaluation of what-if scenarios, for stakeholders with divergent perspectives. The article identifies research challenges to be addressed to enable decision making to support sustainability and provides a map of sustainability modeling issues across disciplines.