Paul (2014, 2015a) argues that one cannot rationally decide whether to have a transformative experience by trying to form judgments, in advance, about (i) what it would feel like to have that experience, and (ii) the subjective value of having such an experience. The problem is if you haven’t had the experience then you cannot know what it is like, and you need to know what it is like to assess its value. However, in earlier work I argued that ‘what it is like’-knowledge comes in degrees, and I briefly suggested that, consequently, some instances of Paul’s argument schema might commit a fallacy of equivocation. The aim of this paper is to further explore and strengthen this objection by, first, offering a new argument—the modelling argument—in support of it, and then by evaluating a range of replies that might be given to this objection on Paul’s behalf. I conclude that each reply either fails or, at best, only partially succeeds in defending some but not all instances of Paul’s argument schema. In closing, I consider how we might revise Paul’s concepts of transformative experiences and choices in response to this conclusion.