Just because one could perform monstrous acts (or attempt them, at least) it didn't mean that they could not feel, like any other human being.
Perhaps Bob's problem was that he could feel his emotions and desires, especially his negative ones, far too intensely: pride, envy, anger, desire for revenge, desire for power, desire for respect and a feeling of accomplishment for doing something, anything. These awful emotions and painful desires he felt utterly consumed Bob, as so many characters of Shakespearean tragedies had become consumed by their fatal flaws.
Sometimes, Bob wondered if his plotting habits could be put to better use, such as plotting out a play instead of an evil plan. His life would make an excellent play.