As we live our lives, we repeatedly make decisions that affect our future circumstances and shape the sort of person we will become. Some of these are major, life-changing decisions. In such cases, we stand at a personal crossroads and must choose our direction. If we make these sorts of life-changing decisions about our futures rationally, can we also make them authentically? In Transformative Experience I argue that, under the most natural and ordinary construal of decisions like this, we cannot. My argument draws on debates in philosophy of mind about how experience is necessary for us to have certain epistemic capacities and cognitive abilities. It also draws on debates about the intrinsic value of subjective color experience, and the importance of the first-personal perspective in understanding the self and its possibilities. I use familiar examples from these classic philosophical debates to raise new questions about experience, its value, and its role in prospectively assessing our first personal futures. Using formal tools drawn from decision theory, causal modeling, and cognitive science, I assess first personal decision making and self-construction in contexts of what I call “transformative decision-making”, a well-defined and—it turns out—very common choice situation in everyday life. In the Afterword, I discuss how the argument has formal applications in and substantive relevance to counterfactual semantics, formal epistemology, and the philosophy of statistics, social science, cognitive science and psychology.