One of my favorite quotes revolves around planning. It came from Helmuth Von Moltke, a 19th century German Field Marshall: “No plan survives first contact with the enemy.”1. The implication here is simple enough: the plan that makes total sense on paper quickly falls apart when confronting the entropy of reality. And yet planning is essential for getting a team moving in the right direction. As Dwight Eisenhower said, “I have found that plans are useless but planning is everything.” And thus we arrive at what I like to call the paradox of planning: planning is the act of creating something that is simultaneously infinitely valuable and completely worthless.