As he grows, so will his ability to think. To rationalize, to set his own achievable goals. Our role will be to help him step out of his comfort zone. To feel the fear and yet know somewhere deep down, “I can do it, I know how to do it.” The idea is to focus not on the Learning, but on the process of Learning. Once a skill is mastered, he will learn to nurture his curiosity, his ability to learn and will challenge himself.
Another way to get your child out of his comfort zone is to always set achievable targets. For the task at hand, what you think he can do will always differ from what he thinks he can do. Let him decide what he can do (at first). Once he achieves it, he knows he can aim for more. Also, it is fruitless to compare what he can do with what other children can do. Others will be better or worse than him. How do you tell him whom to compare to and who not to? Also if you keep comparing him to someone who is better at something is there not a chance of him internalizing that he is not good at anything at all, there is always someone better than him? So, is it not better to compare what he is today with what he was yesterday?
Try it. If you have an infant or young child, you are still ahead in the game. If you have older children, communication, communication and communication will help build trust in the self. You as a parent will do everything to help him go that extra mile but eventually the desire to go that mile has to come from within the child.