Decisions can lead to tremendous change. Edna Ullmann-Margalit and L. A. Paul argue that some decisions lead to a kind of change that we are precluded from rationally evaluating. These are what they call transformative decisions, with typical examples including parenting, college attendance, career pursuits, migration, change of lifestyle, etc. Here we review their challenges to formal models of rational choice, as well as to rationality more generally. We also focus on a few important responses to their work. These range from defenses of formal models to approaches that understand transformation in terms of distinctive kinds of reasons. Additionally, we explore some recent empirical work on transformative decision and how it relates to the normative issues. Finally, there are under explored assumptions framing discussions thus far that we critically examine. It is argued that agents have more resources for evaluating transformative decisions rationally than is assumed by Paul and Ullmann-Margalit. Appreciation of this can open up new avenues of research on transformative decisions going forward.