When trying to explain why our own righteousness, that is the morally upright things that we do, can never be sufficient to please the holy God who created us, I hit upon an analogy that might help some understand what Jesus is trying to say in Matthew 5:20 "For I tell you that unless your righteousness surpasses that of the Pharisees and the teachers of the law, you will certainly not enter the kingdom of heaven." Given that those two groups were believed to be the most righteous people in Israel, the words of Jesus seem like an impossibility. Later on Jesus would explain the failures of the religious leaders of his people, focusing on their pride, failure to care about those in need, and the shallowness of their devotion, but the point about righteousness remains. The statement by Jesus is intended to invoke a sense of despair, about our ability to please God on our own, hence setting aside our pride and allowing us to lean upon the grace of God.
So, how high can we climb on our own, and why isn't that good enough for God? Let's suppose that you make it to the pinnacle of human moral achievement, climbing higher than anyone else.
That seems like a tremendous accomplishment, especially with so many other people falling far short of your lofty achievement and others not even trying. But what is the goal, have you reached it, simply because you can't possibly get any higher?
But God is holy, perfect, without flaw; we are not. Our highest possible ascent toward God, on our own, leaves us far, far short. Could Sir Edmund Hillary have climbed from the summit of Everest into space? Of course not, the gap is too wide, and there's nothing left to climb. Our righteousness, whatever it might be, is equally hopelessly insufficient when compared to the holiness of God.
So, what is left for us to do, give up? In a way yes, to come to God, we need to give up trying to fix ourselves and instead trust that the righteousness of Christ, who died and rose again on our behalf, will be applied to our account by God because of our faith in him. So go ahead and climb the Mt. Everest of morality, doing the right thing is always the right thing, but not because it will make God accept you, do it because you wish to honor the sacrifice of Jesus and be as much like him in this life as possible.
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