I think I understand what you are talking about, and I have the same feeling. Somehow it feels like that when I am thinking or talking about something, I explore the ramifications, consequences of the ramifications, and how I think they will interact and change (with) the other concepts. It requires imagination and a will to let the ideas take you somewhere, instead of trying to control the outcomes based on what you want to believe.
About less wrong/more right: it makes sense. The doctor trying to be "more right" maybe means that he is trying to optimize what makes him successful in his practical life, and understanding the evidence problem simply won't make him more successful. The optimization process, "via positiva", means he just takes what works and optimizes it. Trying to be less wrong is, instead of just optimizing what works, you keep trying new ideas, and instead of optimizing what you already know, you cut off what you know to be false, "via negativa".