This reflective autoethnography illuminates the intricate mechanisms that impact identity construction and deconstruction. Set within the context of football coaching, the author draws upon lived experiences to show his struggle to establish and maintain an identity. By taking the unusual step of exposing his self-doubts and fears, it is the author’s hope that the article will offer comfort to other coaches (and young people in general) experiencing similar difficulties. Signposts are also offered, which direct the reader to the relevant identity literature. Finally, the narrative is evaluated and the benefits to the coaching and psychology communities are discussed.