In Ontario, Canada, early childhood educators are experiencing the beginning of what could be a radical democratic shift in pedagogical thinking and approach for the early years (birth to 6 years). This shift in pedagogy, articulated in the Ontario Ministry of Education’s 2014 pedagogy document ‘How Does Learning Happen?’ (HDLH), acknowledges children, and the adults who live and work alongside them, as curious, capable, and competent creators of culture in democratic society. While this shift has enormous possibilities, the chapter reveals the existing fragmentation between the views articulated in HDLH and the various entrenched organizational and governance structures, policies, and pedagogical practices in Ontario’s early years educational system. In reviewing the situation, the authors draw on the dynamic languages of Complexity sciences and theoretical frameworks to examine the systems active in Reggio Emilia in a search for underlying patterns that might illuminate the challenges in Ontario as attempts are made to enact an early years system that truly embraces a view of children, families, and educators as portrayed in HDLH.