For much of their work, leaders rely on their ability to be clear-eyed, pragmatic, and grounded in the realities of their work. Sometimes, however, leaders must be able to imagine and plan for a world very different for the one that exists now. Today, the world is changing at an unprecedented rate, requiring leaders that can not only adapt to but influence new realities. The capacity to imagine, predict, and understand radical change is essential. Prophetic thinkers envision the potential for historic preservation in creative upheaval, and they become recognized when they are not afraid to think big. They also bring together the most important ideas of history and cultural heritage, often viewed as an “old world” practice, into “new world” endeavors, ensuring cultural heritage is valued in a future heavily based in technological products and leveraging those products to work for the preservation of resources that matter to all segments of our society.