This episode explores the challenges of making decisions about the future, particularly when considering how much we might change as individuals over time. The host interviews philosopher L.A. Paul, who studies transformative experiences and how they reshape our identities. Against this backdrop, the discussion uses the example of John Newton, a former slave trader who underwent a profound religious conversion and became a leading abolitionist, illustrating how dramatically life experiences can alter values and perspectives. More significantly, Paul argues that even seemingly minor experiences can lead to transformative changes, drawing on thought experiments like Mary, a scientist who knows all the facts about color but lacks the subjective experience of seeing it. For instance, the experience of having a child fundamentally alters a person's priorities and values, making it difficult to anticipate future preferences based on current ones. This leads to a discussion of the limitations of simulation in predicting future feelings and the implications for advanced medical directives, suggesting a need for greater flexibility in end-of-life care planning. In conclusion, the episode highlights the inherent difficulty in planning for a future self who may be fundamentally different from the present self, emphasizing the importance of acknowledging this uncertainty in our decision-making processes.