Retirement from sport has the potential to be a major loss for professional athletes. Yet, many athletes resist engaging in career transition planning programs prior to their retirement. This research note reports the findings from an investigation on whether planning for an inevitable resource loss event (i.e., retirement from professional sport) can accrue gains (i.e., sporting performance). Data for this study was sourced from the National Rugby League, a top-level men’s professional sports league in Australasia, and included 28,516 performance selection observations for 632 players over three seasons. The findings demonstrated that higher levels of engagement in preretirement planning were positively associated with team selection, team tenure, and career tenure. Preretirement planning was also found to exert its effect on performance through the experience of career transition practitioners and the number of intervention support sessions the athletes participated in. Results are discussed in relation to conservation of resources and cognitive dissonance theories.