(1) Background: There is abundant literature in talent development investigating the relative age effect in talent systems. There is also growing recognition of the reversal of relative age advantage, a phenomenon that sees significantly higher numbers of earlier born players leaving talent systems before the elite level. However, there has been little investigation of the mechanisms that underpin relative age, or advantage reversal. This paper aimed to investigate (a) the lived experience of relative age in talent development (TD) systems, (b) compare the experience of early and late born players, and (c) explore mechanisms influencing individual experiences. (2) Methods: interviews were conducted with a cohort of near elite and elite rugby union players. Data were subsequently analysed using reflexive thematic analysis and findings considered in light of eventual career status. (3) Results: challenge was an ever-present feature of all players journeys, especially at the point of transition to senior rugby. Psycho-behavioural factors seemed to be a primary mediator of the response to challenge. (4) Conclusions: a rethink of approach to the relative age effect is warranted, whilst further investigations of mechanisms are necessary. Relative age appears to be a population-level effect, driven by challenge dynamics.