Jesus took the man seriously
The rich young ruler came asking what good thing he needed to do to receive eternal life. Jesus first directed him to God's commandments, and named several commands about how people treat one another (Matthew 19:16-19). This was not a casual answer. God's law really is good, and a person who perfectly obeyed it would be righteous.
But that is exactly where the problem lies. None of us has perfectly obeyed God. Paul explains that the law makes sin visible rather than giving sinners a way to make themselves right with God (Romans 3:20). Jesus was not offering an easier route to heaven through effort. He was helping this confident man see what his question had missed.
Therefore by the deeds of the law there shall no flesh be justified in his sight: for by the law is the knowledge of sin.
The man's confidence needed testing
When the ruler said he had kept these commands from his youth, Jesus did not argue about every detail of his past. Instead, he went to the place where the man's devotion was most divided. He told him to give up his possessions, help the poor, and follow him (Matthew 19:20-21).
Jesus was not saying that every Christian must dispose of all property to be saved. He was exposing this particular man's ruling love. The man went away grieving because he had great possessions (Matthew 19:22). His money was not merely something he owned. It had become something he could not surrender, even to follow Jesus.
Jesus said unto him, If thou wilt be perfect, go and sell that thou hast, and give to the poor, and thou shalt have treasure in heaven: and come and follow me.
The commandments reveal the heart
The law reaches deeper than outward behaviour. Jesus had already taught that anger can violate the heart of the command against murder, and lust can violate the heart of the command against adultery (Matthew 5:21-22; Matthew 5:27-28). The ruler may have lived a morally respectable life, yet he still lacked wholehearted love for God.
This is why Scripture says that anyone seeking to be made right by law-keeping must continue in everything the law requires (Galatians 3:10). One failure is enough to show that we need mercy. The commandments are not a ladder we can climb into God's favour. They show us our need for a Saviour.
What Jesus wanted him to see
After the man left, Jesus told his disciples that riches can make entering God's kingdom very hard. The disciples were astonished and asked who could then be saved. Jesus answered by moving the focus away from human achievement and towards God's power (Matthew 19:23-26).
That is the heart of the story. Salvation is God's gift, received through faith, not a reward for a strong moral record (Ephesians 2:8-9). Yet grace does not leave us unchanged. God calls his people to follow Christ, and even prepares good works for them to do (Ephesians 2:10). If this story feels uncomfortably personal, that may be a good invitation to ask honestly: what would be hardest for me to place in Jesus' hands?
But Jesus beheld them, and said unto them, With men this is impossible; but with God all things are possible.