In this article, the authors explore professional identity, multiple roles, and boundary-blurring when working in the sport psychology area with Olympic and Paralympic athletes. Data for this article were collected from case notes, a self-reflective logbook, and supervision sessions during two years before the Games. This study is a tale of a neophyte registered (licensed, chartered) psychologist entering into the high pressure world of international Olympic and Paralympic sports. Key features include how the sport psychologist in the lead-up to the Games can remain grounded in mindful practice and be an island of calm for athletes and coaches in what has to be one of the most stressful sporting events athletes and coaches experience. Dave's (the psychologist's) story illustrates what he and his supervisor believe is the foundation of almost any service—the development and nurturing of caring, holding, loving, attuned, and non-judgmental relationships with athletes and coaches during major international sporting events.