The quest for an active and healthy ageing can be considered a “wicked problem.” It is a social and cultural problem, which is difficult to solve because of incomplete, changing, and contradictory requirements. These problems are tough to manage because of their social complexity. They are a group of linked problems embedded in the structure of the communities in which they occur. First, they require the knowledge of the social and cultural context in which they occur. They can be solved only by understanding of what people do and why they do it. Second, they require a multidisciplinary approach. Wicked problems can have different solutions, so it is critical to capture the full range of possibilities and interpretations. Thus, we suggest that Università Cattolica del Sacro Cuore (UCSC) is well suited for accepting and managing this challenge because of its applied research orientation, multidisciplinary approach, and integrated vision. After presenting the research activity of UCSC, we describe a possible “systems thinking” strategy to consider the complexity and interdependence of active ageing and healthy living.