Organizations that pursue the almost impossible—be it paradigm-shifting theories, scientific breakthroughs, technological invention, disruptive innovation, or game-changing products and services—are constantly grappling with the question, “What should we measure to gauge our potential opportunities, track our progress, or know we’re investing correctly to deliver?” To understand this question, this chapter looks at rising opportunity for businesses to capture breakthroughs and inventions earlier in their development, the transition of the ARPA model (DARPA, I-ARPA, ARPA-E, and ARPA-H) from seeking future results to more near-term impact, and the internal measures used by Lenovo and Facebook to measure their progress. This chapter builds on the pioneering work done in Stanford University’s Foresight program, a two-decade long effort that culminated in the launch of Stanford’s Moonshots program and the book Building Moonshots: 50+ Ways to turn Radical Ideas into Reality.