Militaries are understandably fond of measurements. But today’s world calls for getting in other parties’ heads, which is more ambiguous. It is thus the responsibility of strategic planners to seek out the best ways of developing strategic empathy. The military has turned to social scientists, especially anthropologists, to help it grasp the intricacies of the many ways individuals and small groups form values and make decisions. It is now time to plumb the arts and humanities to see how they teach and express imponderables. It is also time to study historical figures who knew their friends and enemies and to adopt their practices. Instead of confronting great volumes of information, the aim should be to sidestep the noise and select the "chunks" of data that apply best. Complete prediction is impossible; yet military planners must try, and they can improve their chances by reconceptualizing how they predict.