This article provides a neophyte practitioner’s account of providing psychological support to a national team for the first time. The practitioner felt “caught in the headlights” due to their lack of preparation for the range of organizational issues they encountered. In this confessional tale, experiential knowledge gained by the practitioner is shared through the presentation of self-reflections from the 6-month period they supported the squad. While the practitioner’s time with this national squad was limited, it gave him a sense of the micropolitical landscape of the sporting organization and illuminated some of the complexities and dilemmas that characterize applied sport psychology practice. These reflections are offered to guide other aspiring professionals during their initial training experiences.