Someone asked a great question in response to my post last week on Simon the Pharisee:
Much like the two sons in the prodigal son story, how necessary is it to be the younger son to appreciate the Father?
In other words, do we have to sin more grossly in order to be able to comprehend how much we have been forgiven so that we can "love much"?
It seems to me that self-righteousness poses challenges that are similar to wealth in terms of how hard it is to get into the kingdom. If you think you are righteous on your own, you don't believe you need the forgiveness Jesus has to offer. If you are wealthy, you do not need the treasures Jesus has to offer. The poor and the more outwardly sinful often can more clearly see their need for the Savior.
But the wonderful thing about the gospel is that Jesus came to deliver both the prodigals and the older brothers in their respective slavery to sin. It takes a miracle to be delivered from both blinding sinful self-righteousness and blinding sinful indulgence.
One great word of hope for "older brother" types is that the person Jesus chose to write most of the New Testament and to be the great champion of God's grace was Paul, who had excelled all his contemporaries in his "older brotherly" zeal. And one reason I think Jesus did this is to show us that God certainly can help older brothers see how much they have been forgiven and therefore love much (Philippians 3:2-10).
So for all of us relatively well-behaved older brothers: "With man it is impossible, but not with God. For all things are possible with God" (Mark 10:27).