This chapter argues that our inability to anticipate what our future selves, including future selves brought about by?transformative decisions, would be like can often be explained by the same failures of imagination that impede our ability to understand other people. A common sort of such imaginative failure results from our excessive tendency to simulate other people’s subjective perspectives by imagining ourselves in their situation – a strategy easily overused, given our peculiarities and theirs. We have the same tendency with regard to future selves, and so we are forever surprised when our subjective perspective changes significantly – even when we should have known better.