The empirical findings from training transfer research rest on a rather static view of the transfer phenomenon, ignoring potential within‐person change in transfer over time. This study investigates within‐person variability in mastery goal orientation together with variability over time in the application of newly acquired knowledge and skills to the job context. Data from longitudinal surveys of trainees voluntarily attending statistical workshops revealed that trainees varied significantly in 2 characteristics of transfer trajectory: (a) initial attempts to transfer and (b) subsequent rate of change in transfer. Two affective learning outcomes showed differential relationships with transfer trajectories: Whereas posttraining self‐efficacy predicted initial attempt of transfer, motivation to transfer assessed at the end of training predicted subsequent rate of change in transfer. Furthermore, level and variability of trainees’ mastery orientation interacted to influence posttraining self‐efficacy and motivation to transfer, and subsequently transfer trajectories. Specifically, a trainee's mastery orientation level had stronger prediction of these outcomes when his/her mastery orientation distribution was less variable across situations. These findings highlight the importance of attending to within‐person variability in the study of training transfer by (a) considering training transfer as trajectories over time and (b) understanding trainee traits as frequency distributions.