I've come back to this a few times with different thoughts. I wanted to reply with what I really feel about this topic but it also became catharsis at points. As I'm currently undergoing this I understand all too well how proceeding regardless of others' concerns develops one's self.

It's all very good in situations of anger and dispute; when someone blocks your flight with and presents a conflict it is easier to go ahead alone because now it's black and white. You want to move forward but they stand in your path. Regardless of the morality of the decision you are the protagonist and they the antagonist and you fight for your corner and they for theirs.

I think this is similar to rboone's situation. There's a group of people doing X or doing X in a certain way and so he does Not-X. Where he can, he does the most extreme not-X he can find and is tolerable to him. He sees the other side and he sees if he likes it. People frequently live like pendulums, swinging back and forth from extreme position to less extreme position until they find a point in the middle they like. I agree, this healthy. His message to the world? "Try the black side of your black-white divide, why is that side so wrong to you? " He wants to be free of the Us Versus Them culture that refuses to believe the enemy might have a valid point of view. I enjoy trying to see the point of view of other people and struggle greatly when I cannot appreciate what they're saying, but I think for all rboone's chastisement of the black-white man he suffers from much the same. The issue is not that we refuse to appreciate the other person's side, but that we believe these sides exist as true or false.

Suppose someone blocks your flight with not anger but tears. Where they cry and say "If you think this is something you have to do". There isn't a big-bad standing in front of you. You can't do not-X of what they're doing. The obstacle to your flight isn't them anymore, but the suggestion that your own decision might be wrong and the pain you cause might be greater than what you thought. This is everyone who's moved their family for their job. Then they stand at your side telling you that the enemy that prevented your movement either isn't them anymore, or wasn't ever them. You'll hurt them by moving forwards, but you think you'll hurt yourself if you don't move forward. In most of the "black and white" situations the big bad never existed, but right now you can't even pretend it did. It's just you standing up against yourself saying "Well, what's blocking you? Go or don't, but do something."

This is my shade of grey. Decisions that are entirely yours and you could conceivably be completely wrong and cause pain for no reason. You don't actually know if you'll do better if you move forward and you don't know if you'll do better by not taking the decision. That's where I believe true personal development comes from because it's hard and it means relying entirely on yourself. At this point you can't even rely on idioms. "You miss every shot you don't take". What if each shot you take comes at a cost. An action is both doing X and not doing X, and not doing something is no less or more difficult than doing something.