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This paper explores the idea of the prudent entrepreneurial self, through re-conceptualizing prudence into the domain of entrepreneurial education, to unite the two processes of becoming enterprising and entrepreneurial. It is argued that developing a capacity for prudence among graduates involves past, present and conjecture forms of knowledge that the authors find in the interplay between individuation and social awareness.

Building on Palmer's idea of wholeness, the authors discuss six poles of paradoxes in entrepreneurial education and in conjunction establish a philosophical argument for the idea of stimulating the development of prudence as fundamentally important to contemporary notions of entrepreneurial education.

The paper presents a model to develop a schema that moves students towards becoming prudent entrepreneurial selves. The model rests on two interrelated developmental processes – individuation and social awareness – conditional for developing the three forms of knowledge (past, present and conjecture) that makes up prudence where developing prudence is a means to handle or cope with the unknown.

This paper argues that for enterprise and entrepreneurship education to realize their potential contributions, both the relationships between each field and the overarching purpose that ties the fields together need to be rethought, and the poles of paradoxes need to be connected to further develop both fields and creating wholeness for the emerging scholarly discipline.

To educate towards the prudent entrepreneurial self means educating towards an unknown end where student development aims to meet both the objectives of individual development and the growth in social awareness required to handle the changing nature of contemporary society.

This study philosophically conceives a united enterprise and entrepreneurship education landscape in which deeper student learning makes possible the notion of the prudent entrepreneurial self.