There are unique moments in curriculum development when an opportunity for a fresh start or a major turn in design fl eetingly presents itself. These moments opened up in different locations across McMaster University at different times and eventually led to several quite different initiatives in inquiry-guided learning (IGL). Well-travelled pedagogical ideas combined with administrative openings and faculty interest to foster IGL within and across disciplines. Bell's work on general education (Bell, 1966), along with the ideas of self-directed learning described by Knowles (1975) and Candy (1991), were infl uential during the early stages of IGL. Pockets of experimentation in collaborative self-directed learning emerged across the campus over a thirty-year period. An institutional culture that prized risk taking and innovation nurtured these experiments.But innovation does not occur in a vacuum. Traditional teaching methods that emphasized disciplinary content, along with a reward system that emphasized research over teaching, posed significant challenges. And administrators had to be convinced that it was worthwhile to allocate budget items to ill-defi ned pedagogical initiatives. In this chapter, we discuss some of the enabling factors that helped to encourage early experimentation in IGL and push it toward greater institutionalization, as well as some of the challenges and obstacles that had to be overcome (see Figure 9.1). Although higher education institutions are diverse, each with their unique Over the past thirty years, inquiry-guided learning has fl ourished at McMaster University. In this chapter, we discuss some of the enabling factors that helped to encourage early experimentation in inquiry-guided learning and push it toward greater institutionalization as well as some of the challenges and obstacles that had to be overcome.