Risk is inherent to many, if not all, transformative decisions. The risk of regret, of turning into a person you presently consider to be morally objectionable, or of value change are all risks of choosing to transform. This aspect of transformative decision-making has thus far been ignored, but carries important consequences to those wishing to defend decision theory from the challenge posed by transformative decision-making. I contend that a problem lies in a common method used to cardinalise utilities – the (...) von Neumann and Morgenstern (vNM) method – which measures an agent's utility function over sure outcomes. I argue that the risks involved in transformative experiences are constitutively valuable, and hence their value cannot be accurately measured by the vNM method. In Section 1, I outline what transformative experiences are and the problem they pose to decision theory. In Section 2, I outline Pettigrew's (2019, Choosing for Changing Selves) decision-theoretic response, and in Section 3, I present the case for thinking that risks can carry value. In Section 4, I argue for the claim that at least some transformative experiences involve constitutive risk. I argue that this causes a problem for decision-theoretic responses within the vNM framework in Section 5. (shrink)