This article explores the various elements of Canadian educational entrepreneurialism as manifested yesterday, today, and tomorrow and in relation to the social and political influences of the time. This discussion is informed by the findings of the International Study of the Preparation of Principals (ISPP) and represents an expansion of the dimension of boundary-breaking entrepreneurialism contained in the Life Long Learning Leader (4L) leadership development framework. The showcasing of entrepreneurialism in Canada is offered in an attempt to advocate for and to demystify the dimensions of principled and socially responsible educational entrepreneurship needed by tomorrow's leaders. The article closes with conclusions intended to inform leadership development in other cultural contexts. (Contains 3 tables and 1 figure.)