What Does True Righteousness Look Like?
A conversation on the Sermon on the Mount
Today we are continuing our processing of the Sermon on the Mount.
We started off by working our way through the Beatitudes, where Jesus flips blessing upside-down. Blessing is not just getting what you want or being free of stress and pain or having everyone like you. Blessing is beyond circumstances and situations. It’s in relationship with God.
You’re blessed when you know you need God. God comforts those who are hurting. Gentle people will inherit what truly matters. Longing for what’s right brings satisfaction. Show mercy and you’ll receive mercy. A clean heart helps you see God clearly. Making peace shows you belong to God’s family. Being mistreated for doing right brings heaven close. Rejoice when you're mocked for following Christ—your reward is great.
Then last week we jumped out of the beatitudes into Jesus’ calling us to be salt and light. We saw that we are valuable to God, that relationship with God is valuable, and that our connecting people to relationship with God is valuable.
“let your light shine before others, that they may see your good deeds and glorify your Father in heaven.” (Matthew 5:16b)
And now we come to the hinge or pivot point of the Sermon on the Mount.
As Jesus continues in His message, He will state incredible expectations that move righteousness from being an external thing to being an internal transformation. And this transformation can’t happen just through willpower. Willpower and religiosity won’t cut it. Grace is needed.
Today we will see Jesus drop the bomb on this listeners as He says:
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. (Matthew 5:20)
The Pharisees were religious teachers, experts in Jewish law and Scripture. They taught people how to live according to the Torah (the first five books of the Bible). They were generally popular with the people, having a strong connection with everyday Jewish people. They taught in synagogues and focused on how regular people could live holy lives. The Pharisees were middle class; unlike the Sadducees who tended to be of the elite rich, the Pharisees were more “of the people” people.
The Pharisees were also strict rule followers, emphasizing following not just the written laws of Moses but also oral traditions—extra rules meant to help people avoid sin. They often Clashed with Jesus, who challenged the Pharisees for being hypocritical—looking good on the outside but lacking mercy, justice, and love in their hearts. Not all of them were bad; some Pharisees, like Nicodemus and Gamaliel, were open to Jesus or defended fairness. Many early Christians (like Paul) even came from the Pharisee movement.
So when Jesus said, unless your righteousness surpasses that of the Pharisees, the collective response had to be, WHAT??
So we are going to dig into that and process together. Our first step today is to think about what makes a good person. Work with the people around you to make as long of a list as you can in the next couple of minutes.
What makes someone a good person?
Now look at your list together and talk about this:
What makes someone stand out to you, for better or worse?
Righteousness. Some people stand out as being righteous. But what would nudge or encourage someone to be extra righteous?
There are some things that don’t really work: yelling, guilt-tripping, nagging, shaming, threatening, lecturing, using sarcasm, manipulating, comparing, controlling… But what does work? That’s a complicated question.
When I think of an unusual moment in the Bible, featuring a change of heart leading to doing what is right, I think of the narrative found in Numbers 22. As we pick up the story, the Israelites are near the end of their 40-year wilderness journey.
Then the Israelites traveled to the plains of Moab and camped along the Jordan across from Jericho. Now Balak son of Zippor saw all that Israel had done to the Amorites, and Moab was terrified because there were so many people. Indeed, Moab was filled with dread because of the Israelites. The Moabites said to the elders of Midian, “This horde is going to lick up everything around us, as an ox licks up the grass of the field.”
So Balak son of Zippor, who was king of Moab at that time, sent messengers to summon Balaam son of Beor, who was at Pethor, near the Euphrates River, in his native land. Balak said: “A people has come out of Egypt; they cover the face of the land and have settled next to me. Now come and put a curse on these people, because they are too powerful for me. Perhaps then I will be able to defeat them and drive them out of the land. For I know that whoever you bless is blessed, and whoever you curse is cursed.”
The elders of Moab and Midian left, taking with them the fee for divination. When they came to Balaam, they told him what Balak had said.
“Spend the night here,” Balaam said to them, “and I will report back to you with the answer the Lord gives me.” So the Moabite officials stayed with him.
God came to Balaam and asked, “Who are these men with you?” Balaam said to God, “Balak son of Zippor, king of Moab, sent me this message: ‘A people that has come out of Egypt covers the face of the land. Now come and put a curse on them for me. Perhaps then I will be able to fight them and drive them away.’”
But God said to Balaam, “Do not go with them. You must not put a curse on those people, because they are blessed.”
The next morning Balaam got up and said to Balak’s officials, “Go back to your own country, for the Lord has refused to let me go with you.” So the Moabite officials returned to Balak and said, “Balaam refused to come with us.”
Then Balak sent other officials, more numerous and more distinguished than the first. They came to Balaam and said: “This is what Balak son of Zippor says: Do not let anything keep you from coming to me, because I will reward you handsomely and do whatever you say. Come and put a curse on these people for me.”
But Balaam answered them, “Even if Balak gave me all the silver and gold in his palace, I could not do anything great or small to go beyond the command of the Lord my God. Now spend the night here so that I can find out what else the Lord will tell me.”
That night God came to Balaam and said, “Since these men have come to summon you, go with them, but do only what I tell you.”
Balaam got up in the morning, saddled his donkey and went with the Moabite officials. But God was very angry when he went, and the angel of the Lord stood in the road to oppose him. Balaam was riding on his donkey, and his two servants were with him. When the donkey saw the angel of the Lord standing in the road with a drawn sword in his hand, it turned off the road into a field. Balaam beat it to get it back on the road.
Then the angel of the Lord stood in a narrow path through the vineyards, with walls on both sides. When the donkey saw the angel of the Lord, it pressed close to the wall, crushing Balaam’s foot against it. So he beat the donkey again.
Then the angel of the Lord moved on ahead and stood in a narrow place where there was no room to turn, either to the right or to the left. When the donkey saw the angel of the Lord, it lay down under Balaam, and he was angry and beat it with his staff. Then the Lord opened the donkey’s mouth, and it said to Balaam, “What have I done to you to make you beat me these three times?” Balaam answered the donkey, “You have made a fool of me! If only I had a sword in my hand, I would kill you right now.”
The donkey said to Balaam, “Am I not your own donkey, which you have always ridden, to this day? Have I been in the habit of doing this to you?” “No,” he said. Then the Lord opened Balaam’s eyes, and he saw the angel of the Lord standing in the road with his sword drawn. So he bowed low and fell facedown.
The angel of the Lord asked him, “Why have you beaten your donkey these three times? I have come here to oppose you because your path is a reckless one before me. The donkey saw me and turned away from me these three times. If it had not turned away, I would certainly have killed you by now, but I would have spared it.”
Balaam said to the angel of the Lord, “I have sinned. I did not realize you were standing in the road to oppose me. Now if you are displeased, I will go back.” The angel of the Lord said to Balaam, “Go with the men, but speak only what I tell you.” So Balaam went with Balak’s officials.
When Balak heard that Balaam was coming, he went out to meet him at the Moabite town on the Arnon border, at the edge of his territory. Balak said to Balaam, “Did I not send you an urgent summons? Why didn’t you come to me? Am I really not able to reward you?”
“Well, I have come to you now,” Balaam replied. “But I can’t say whatever I please. I must speak only what God puts in my mouth.” Then Balaam went with Balak to Kiriath Huzoth. Balak sacrificed cattle and sheep, and gave some to Balaam and the officials who were with him. The next morning Balak took Balaam up to Bamoth Baal, and from there he could see the outskirts of the Israelite camp. (Numbers 22:1-41)
Now, the story is not over. Balaam didn’t curse the Israelites:
First Oracle – “How can I curse whom God has not cursed?” (23:8)
Second Oracle – “God is not a man, that he should lie... he has blessed, and I cannot change it.” (23:19–20)
Third Oracle – Balaam blesses Israel again, describing their future prosperity and security. (24:5–9)
Fourth Oracle – He even prophesies the downfall of Moab and other nations. (24:17–24)
But feel this: at the beginning, Balaam resolves to do what is right. He is tempted to go outside of what God wants, but he is still resolved… but his internal must have been shifting. And God sees!
We are going to take a moment for a would you rather question, just for fun.
Would you rather have to tell everyone exactly what you're thinking—or never be able to communicate your thoughts at all? Why?
The story shows that God knew Balaam’s heart. And Balaam went from listening to God to not seeing the consequences that were right in front of him. And in this story, the donkey saw and tried to help—and even as Balaam was in the middle of an actual conversation with a donkey, Balaam was still oblivious, until finally God opened his eyes and he saw the angel of the Lord poised to strike him down.
Now, this is an easy moment to pick on Balaam, but don’t we all have the ability to be oblivious? Let's talk this out a little:
What are some things that can cause a person (even me) to miss why something is right or wrong, good or bad, God’s will or not?
Jesus in Matthew 5 says,
“Do not think that I have come to abolish the Law or the Prophets; I have not come to abolish them but to fulfill them…. 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.” (Matthew 5:17, 20)
The Pharisees had a form of righteousness—also known as self-righteousness. We’ve referred frequently to this parable that Jesus shared in Luke 18:
To some who were confident of their own righteousness and looked down on everyone else, Jesus told this parable: “Two men went up to the temple to pray, one a Pharisee and the other a tax collector. The Pharisee stood by himself and prayed: ‘God, I thank you that I am not like other people—robbers, evildoers, adulterers—or even like this tax collector. I fast twice a week and give a tenth of all I get.’ But the tax collector stood at a distance. He would not even look up to heaven, but beat his breast and said, ‘God, have mercy on me, a sinner.’ I tell you that this man, rather than the other, went home justified before God. For all those who exalt themselves will be humbled, and those who humble themselves will be exalted.” (Luke 18:9-14)
Earlier we built a list of “What makes someone a good person?” Now let's bring this to our table: while righteous and self-righteous may look similar externally, how are they different internally?
Righteousness quietly gives without needing recognition; welcomes questions and doubts with grace; admits fault and seeks growth; defends the dignity of others, even those they disagree with; prays out of longing and trust; feels conviction and moves toward repentance; lives with humility and curiosity; sees everyone as equally in need of grace; loves God and neighbor as a response to grace; and obeys from the heart.
Self-righteousness posts every act of kindness on social media; needs to have all the right answers—and make sure you know it; always has a reason why they’re not wrong; only shows compassion to people who “deserve it”; prays to appear spiritual or to impress; justifies every action and deflects correction; lives with pride and superiority; sees some people as beneath them or too far gone; tries to earn God’s love and prove they’re better than their neighbor; and obeys out of fear, pressure, or image.
How are righteousness and self righteousness different internally?
Now Paul, one of the New Testament authors, knew both sides of this divide, having been both a religious authority (self-righteous) and a humble follower of Jesus (needing and celebrating grace). Let me plant some verses he wrote in our minds and then invite you to process together.
for all have sinned and fall short of the glory of God, and all are justified freely by his grace through the redemption that came by Christ Jesus. (Romans 3:23-24)
For it is by grace you have been saved, through faith—and this is not from yourselves, it is the gift of God—not by works, so that no one can boast.(Ephesians 2:8-9)
he saved us, not because of righteous things we had done, but because of his mercy. He saved us through the washing of rebirth and renewal by the Holy Spirit, whom he poured out on us generously through Jesus Christ our Savior, so that, having been justified by his grace, we might become heirs having the hope of eternal life. (Titus 3:5-7)
I do not set aside the grace of God, for if righteousness could be gained through the law, Christ died for nothing! (Galatians 2:21)
How does God’s grace impact righteousness?
Okay, today we have listed what makes a person good, asked what makes a person stand out, talked about our obliviousness, and smashed grace and righteousness together. Now, let’s end with one final discussion.
Why is righteousness valuable?
Take It Deeper Questions
Read Matthew 5:17-20.
As a child, what rules did you think were unreasonable? Has your perspective changed at all as you have aged?
What is the connection between grace and righteousness?
How does a person obtain a righteousness that surpasses that of the Pharisees? What is the challenge? What is the Good News?
How are you encouraged, focused, challenged and/or confused by this text?
Bible Reading Plan
Exodus 20 • The Ten Commandments
Deuteronomy 6 • Love the Lord your God
Jeremiah 31:31–34 • The New Covenant
Romans 8 • The Law fulfilled in us
Galatians 3 • Law and faith
Hebrews 8–10 • Christ’s fulfillment of the law