What is strategic foresight and why does it matter? What role does hindsight play in it? Why are individuals, organizations and societies continually surprised by un-foreseen events? The purpose of this research monograph is to deepen understanding of the role that hindsight plays in strategic foresight. By doing so, the intention of the book is to offer some insights into strategic foresight failures. Drawing on received research in strategy, psychology, philosophy and history, the role of counter-to-factual reasoning as a heuristic device is discussed and analysed as a way of rediscovering the complexity of the past. The judicious use of such a heuristic device as counterfactual reasoning, both as a sense-making process and as a strategic planning analytical framework, the book concludes, is a process for re-discovering the past, identifying the driving forces underpinning the emergence of startling patterns and fortifying strategic foresight processes.