Both becoming and unbecoming an elite athlete is a complex endeavour filled with mixed feelings and emotions some of which are related to certain moral and ethical dilemmas. Drawing on the Ancient Greeks’ emphasis on the aesthetics of existence, Foucault (1985), invited us to focus on the production or shaping of an ethical self through a restrained and stylised engagement with problematized activities. In this chapter I present a narrative that delves into my creation of a post elite athlete self as a work of art (Foucault, 2000) in relation to (elite) sporting practices. The narrative covers the period from my last years of playing tennis at an elite level, first years of playing the game socially and being a coach to reinterpreting my athlete self as a critical scholar, and negotiating my critic and complicit elite athlete self when engaged in my own kids’ sport and everyday leisure time activities. The narrative reveals how I am engaged in a protracted process of ethical self-creation involving extended periods of ambiguity and uncertainty. Through my narrative I further highlight how problematizing normalised practices that are tied to pleasure, success, reward and power are difficult even when these practices are known to create various problems. In negotiating disciplinary technologies and discourses of performance, competition and winning I argue that I will to some extent always have a desire to adhere to these notions. In my post elite sporting life, they are still and will probably always be tied to the pleasures and displeasure I derive from participation in sport and other leisure time activities. The chapter concludes with a discussion of how Foucauldian analyses of athlete narratives can help provide a moderate critique of elite sport practices and some final thoughts on my ongoing negotiation of the critic and complicit elite sporting self.