In this chapter, we explore the use of psychoanalysis as a tool to gauge the impact of assessment and selection in mathematics on individuals in terms of their shifting ‘internal’ positioning in response to the experience of being judged and/or chosen, one that is central to an education in mathematics. In doing so, we present extracts taken from three of our ‘mathematics biographies’, narratives of our relationships with mathematics. We wrote them independently, circulating them only when all the stories were complete. When ‘unveiled’, they showed striking similarities in their presentation of ambivalences and their references to structural and personal comparison and competition, and to mathematics as a mediator of relationships with self and other/s. In this chapter, we make sense of them as accounts of defended subjects, selves ‘forged out of unconscious defences against anxiety’ (Hollway & Jefferson, 2000, p. 19), while also recognising the role of discourses in our defences. Following Wendy Hollway and Tony Jefferson (2000), we argue that ‘subjects invest in discourses when these offer positions which provide protections against anxiety and therefore supports to identity’ (p. 21). In an environment where selection and assessment are powerful markers of who we are, this psychosocial approach can give us new understandings of the pain, pleasure, and power in our relationships with mathematics, providing a critique of current practices.