In this paper the efforts of transforming ‘regular’ entrepreneurship to a specific kind of ‘entrepreneurial self’ in education are linked to the materialization of employability. It will be illustrated that schoolchildren, under the guise of entrepreneurship education, are taught how to work on improving their selves, emphasizing positive thinking, the joy of creating and awareness of the value of their own interests and passions. This ethic reminds us that we can always improve ourselves, since the enterprising self can never fully be acquired. The flipside of this ethic is that, by continuously being encouraged to become our best, it may be difficult to be satisfied with who we are. Highlighted in this paper is that, with all the amusement and excitement present in entrepreneurship education, also comes an expectation of the individual to fight against all odds. Recruiting students to this kind of shadow-boxing with their selves should involve critical reflection on its political dimensions, human limits, alternative ideals and the collective efforts that are part of entrepreneurial endeavours.