Drawing on Berlant’s concept of cruel optimism, the chapter explores entrepreneurial attachment to success ethics (a system of legitimation that prioritizes norms and actions consistent with institutionalized notions of success) (Berger & Luckmann, 1966) generated by a cluster of promises afforded by the enterprise culture. Based on five life stories of entrepreneurs who had first-hand experience of bankruptcy, this chapter aims at gaining a more nuanced understanding of why the uniformity and orthodoxy of identities around an entrepreneurial ideal persist and grow in the context of entrepreneurial failure. The chapter is motivated by an interest in the human consequences of bankruptcies and focuses on exploring how the appropriation and internalization of social norms propounded by the enterprise culture might fix life narratives in a way that hinders the very possibility of identities that are ‘more sensitive to themselves’ (Cohen, 1992, p. 178). Firstly, the chapter highlights the strength and endurance of the attachment to these principles even in the face of the totality of bankruptcy loss and extreme disruptions to the emancipatory dream. Secondly and relatedly, the chapter examines how failure may strengthen the optimistic nature of the entrepreneurial attachment to success ethics. We argue that continuous participation in enterprise culture is central to the construction of entrepreneurial subjectivity as it provides a sense of proximity (Ahmed, 2010) to the ‘right’ values – values that arguably contain the promise of success, status and future. To understand participants’ attachment to extremely stressful, and often traumatic, entrepreneurial lives and their propensity to promulgate and reproduce the entrepreneurial ideal, we need to think about social norms related to the entrepreneurial ideal not only as aspirational but also as redeeming and reassuring about the present and future experience of social belonging that can be lived in affective transactions that take place alongside the more instrumental ones (Berlant, 2011).