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In the interest of developing sustainability practitioners, this manuscript challenges the conceptualization of transformative learning for Education for Sustainability (EfS) in relation to single courses or programs. Conversely, I will argue that becoming a sustainability practitioner (i.e., someone who takes action in the interest of the sustainability movement) is life-long and life-wide commitment. Time and how and why it matters is addressed. To develop this point, this manuscript details a case study of an education for sustainability graduate program that I designed and currently lead. The purpose is to further theorize transformative learning as it links individual action(s) and collective change(s) in the border-like but permeable spaces that are in-between. It asks the practical question of the ways educators (and practitioners) might expansively and generatively work together in creating a lifetime of classrooms to continuously bridge individual action and collective change.