This study seeks to extend the variety of written methods used in sport and exercise research by outlining the use of a novel written technique for data collection: ‘a letter to my younger self’. The use of solicited letter writing has long been endorsed as a valuable technique as part of the therapeutic process, but has yet to be considered as a method of collecting qualitative data. In this study, 21 participants who had experienced chronic pain while playing sport were invited to write a letter back to their younger self. A dialogical narrative analysis was used to analyse the written letters and our results are presented in two forms. First, a ‘collective letter’, written using amalgamated participant quotations. Second, an accompanying commentary which illustrates the characterisations, structure, and narrative themes that were evident in the data collected. Our findings extend existing knowledge of chronic pain in sport, contrasting previous literature that has presented degenerative stories. Further, we also illuminate the danger of the performance narrative in privileging personal agency and the risks this poses to receiving support during chronic pain. We conclude by challenging researchers to consider the importance that should be attributed to hindsight and the value of re-describing experiences with wisdom and knowledge of the significance of the past.