Have you ever thought about what the rich young man was lacking in the Gospels? He was filled with so much enthusiasm that he ran up to Jesus to ask Him one question, "what shall I do that I might receive life everlasting?" What is at the heart of this question? The young man understood that eternal life was a gift, first of all, something to be received. He grasped the concept that we can't simply float through life, but must strive after holiness--it doesn't just appear overnight. He lastly must have had some sort of dissatisfaction and unfulfilled longing that he knew would not be satisfied without Our Lord.
Now, where did the disconnect occur?
Our Lord sees the rich man's generosity, loves him, and asks him to trust in Him more than he trusts in his own riches. For the dialogue follows with Jesus telling the crowd, "how hard is it for them that trust in riches, to enter into the kingdom of God?" The young man was unwilling to take a risk. The greatest that this world could offer was already his--he "had great possessions." But they had ensnared his heart. Earthly security was laid on the scale alongside trust in God, or you could say that on one side was sadness and the other joy, for he "was struck sad," and was willing to walk away from the Source of all joy.
I wonder if he wanted Our Lord simply to tell him that he was doing enough. Or maybe it was the part of the question he asked, "what shall I do?" For Our Lord tells us that it's impossible for men, but not with God. Maybe the better question for him to ask would have been, "Lord, how can Thy will be fulfilled in me, such that I may enter eternal life with Thee?"
Are we willing to follow Him? Are we willing to trust Him? Trust Him enough to risk everything else?