According to L. A. Paul, the subjective value of an outcome is normally assessed by running a cognitive model of what it would be like if that outcome were to occur. However, cognitive models, along with the expectations in which they result, are unreliable for application to transformative experiences because we cannot know what it would be like for an outcome to occur if we have never experienced it before. This paper argues that despite their unreliability, expectations are still important in the case of chosen and unchosen transformative experiences because expectations about an outcome can systematically influence the very experience of that outcome. More precisely, empirical research shows that affective experiences tend to assimilate to affective expectations. In turn, more positive affective experiences lead, ceteris paribus, to higher subjective value. Therefore, rational agents confronting transformative outcomes should form or cultivate positive/optimistic affective expectations since, all else being equal, that maximizes subjective value.