Charlie Joffe said to me, in an offhand way one day, "The winner in any negotiation is the first person who's willing to be outrageous." And I would submit to you that the person who pushes the ball the furthest up the mountain creatively in terms of art, or craft, or whatever it is that we do for a living, is the first person who's willing to be outrageous. – Glenn Gordon Caron, in On Writing #11
Well, but only if you are willing to define not making a deal as winning. It's certain that you can't usually get what you want unless you're willing to walk away. (In poker, you can't win a single hand unless you're willing to go to the river at least some times. That's what makes people reluctant to bet against you. If they know you'll fold it costs them nothing to raise.)
But if you're never willing to be outrageous, well, you're not going to make anything new. As Shaw said:
The reasonable man adapts himself to the world; the unreasonable one persists in trying to adapt the world to himself. Therefore all progress depends on the unreasonable man.