Research investigating the challenges experienced by high-performing athletes throughout development has predominantly used retrospective designs. Consequently, there is limited empirical and prospective data to inform the temporal dimensions of these experiences and their perceived impact on development. Therefore, this investigation sought to prospectively explore the temporal impact of perceived challenges on the development of six national-level youth footballers during their entrance into, and first season in, a selective national talent development environment. Participants engaged in monthly semi-structured interviews over a season, with data analysed using Reflexive Thematic Analysis. Findings demonstrated that each player’s experience in the national system was characterised by exposure to significant biopsychosocial challenges. The dynamics of these challenges were highly individualised, with variations in the temporal nature, emotional disturbance, and the psycho-behavioural skills deployed to navigate such challenges. Within the national system, the perceived judgement and the ongoing selection and deselection processes were a pervasive feature of each player’s experience, presenting significant challenge across the season. Yet, the temporal impact of this challenge varied among players. In practice, we advocate for talent systems to adopt a personalised approach to managing challenges faced by athletes and to recognise the individualised nature of the temporal impact of such challenges.