This paper provides athlete and practitioner insights regarding a novel coping-oriented personal-disclosure mutual-sharing (COPDMS) intervention developed and administered in a youth soccer context. Participants were 18 male soccer athletes (mean age 17.29 ± 0.73 years) who belonged to the same professional academy in England. The COPDMS intervention comprised an initial sport psychology education session (Week 1), a session introducing COPDMS (Week 2), a COPDMS session (Week 4), and a follow-up session (Week 9). During the COPDMS session, athletes mutually shared personal stories and/or information about transitions as they approached a time when they would gain a professional contract or would be released from their soccer academy. Athletes communicated a range of contextually relevant demand and resource appraisals during the COPDMS session. Several athlete and practitioner insights about the COPDMS process and outcomes were provided that can guide future researchers and practitioners seeking to develop and deliver bespoke PDMS interventions in sport.