My theory is that people have been trained and rewarded for being “not wrong”. Strategy requires you to take a stance and get specific. Sometimes the strategy will not work.

I think we need to do a better job of encouraging this sort of thinking. I don’t remember where I heard but it was something along the lines of “we tell kids they can be whatever they want and then actively discourage them when they take the necessary steps to do those things by operating outside the box”. So this type of thinking becomes normal. Then when it comes to strategize people try to follow “best practices” and “proven techniques” which is kind of the opposite of strategy.