What is Santiago's biggest fear?
As Santiago's character is developed more, the fears he holds become more complex. They are the type of fears that strike at not merely his being, but at the condition of all human beings. For example, one of Santiago's biggest fears is whether or not he is denying his own opportunity to embrace something larger or grander in his life. While he knows being a priest would make his father happy and would conform to what social expectations around him, Santiago understands that this is not going to make him happier. This is not going to yield something more worthwhile in his being. One of Santiago's biggest fears is that he will not achieve this condition of being. Santiago realizes that there is a fear in not being what he can be, but rather acquiescing to what he is presumed to be.
From this point, Santiago generates his biggest fear as one of failure. The fear of failure dominates Santiago's being. It is one in which Santiago must learn to let go in order to find greater success. For Santiago, this is something that becomes larger than life for him. Santiago's fear of failure comes to represent one of his biggest fears. Failure means the repudiation of Santiago's purpose of being. Through a combination of self- reliance and understanding help from others, Santiago learns to overcome this fear as he strives for his Personal Legend. In both fears, one recognizes the fears that are intrinsic to being in the world. Santiago understands clearly that great risk taken in accomplishing his Personal Legend is accompanied by the fear of failure and of breaking the conformist mold. Both fears operate in tandem as his biggest concerns in his journey or quest.