Fine arts organizations and practitioners face tremendous challenges in the twenty-first century created by changing demographics, shifting global economic realities, the rapid diffusion of digital technology, new patterns of audience engagement, and cultural shifts within institutions, among others. These new realities are forcing fine arts and culture entities at all levels within the sector to reconsider their models, policies, practices, behaviours, and structures. This research is intended to provide an analysis and critical overview of the state of the fine arts and culture sector in Canada while also aiming to illuminate ways in which change might happen in the sector. This research takes a systems view of the relationships between primary stakeholders, first examining some of the key challenges facing the sector today and then uncovering the system structures and archetypes supporting the status quo. Ultimately, this research endeavours to illuminate new strategies to supporting a resilient, thriving fine arts and culture sector in Canada.