> In war, lack of preparation means death of your men at minimum, and the collapse of your nation at worst.
This is the fallacy that keeps people locked in over preparing. The way past it is to identify less risky goals that are still aligned with that particular objective. So in war your objective is to learn the enemy's weaknesses. So you could try trading with them, to survey their defenses. Imagine the Vikings at Lindisfarne, they are not going to go in blind. They first build a trading relationship, selling fish, and as friends they can see how strong the Abbey is, how many monasterial guards there are, or when the collection trays are the most full etc. Very little risk right? Similarly with sales, where your risk is your reputation. Say, you can't afford to jeopardize it with your one big connection because you spent a decade building the relationship. Well then you go in asking for advice on your idea, something low risk, instead of trying to make a yes-no sale.