An Entire Life of Repentance

Repentance is a central doctrine in the Christian faith. One of the most common ways you will hear Christians talk about repentance is as a “turning around”. You may have even seen an illustration of a person walking along a path of sin, and repentance is the action of stopping and turning around to walk back in the direction of God.

Sin is often described as breaking God’s commandments, and so when we put these two ideas together our understanding of repentance includes feeling remorse about our sin and “turning around” our sinful behaviour into righteous or moral behaviour.

These concepts of sin and repentance are both true, but I would caution that this simple understanding of repentance can lead you to believe that repentance is an act of your own will that you do at various moments in your life. As you will see today, Jesus’ words take us much deeper.


Did you know that the first of Martin Luther’s 95 theses—famous for kicking off the Protestant Reformation—read “Our Lord and Master Jesus Christ willed the entire life of believers to be one of repentance”? One’s entire life. Not just a moment here and a moment there, and not an act of your own will, but a life-long, ongoing state of being. That’s a different way to think about repentance isn’t it?

Today I want you to grow in your understanding of what an entire life of repentance looks like. We will do this through a study of two main characters in Jesus’ world: the tax collector and the Pharisee. Let’s start off with our passage for today, Matthew 21:28-32. To set this up, Jesus is in the temple courts and speaking to a group of chief priests and elders.

“What do you think? There was a man who had two sons. He went to the first and said, ‘Son, go and work today in the vineyard.’

‘I will not,’ he answered, but later he changed his mind and went.

Then the father went to the other son and said the same thing. He answered, ‘I will, sir,’ but he did not go.

Which of the two did what his father wanted?”

“The first,” they answered.

Jesus said to them, “Truly I tell you, the tax collectors and the prostitutes are entering the kingdom of God ahead of you. For John came to you to show you the way of righteousness, and you did not believe him, but the tax collectors and the prostitutes did. And even after you saw this, you did not repent and believe him.

Jesus makes a very clear and distinct contrast in this passage. The tax collector is entering the Kingdom of God and the Pharisees are not. Why is this? Well, we have a hint here in Jesus’ reference to John the Baptist preaching about “the way of righteousness”. If you flip over to Matthew 3:2 and 4:17 you will read that the way of righteousness, as taught by John, was the way of repentance. So if we want to understand more deeply what it means to say that your entire life is a life of repentance, we can look more deeply at the lives of the Pharisee and the tax collector, which Jesus contrasted in this passage.


Let’s start with the Pharisee. In Jesus’ time Jewish religion was rooted in the temple and the Torah. The temple was the heart of worship and ritual. Priests were involved in temple operations, they ran festivals and sacrifices and prayer. The Torah, also called the law or religious teaching, was the five books written by Moses. There was also a great deal of oral commentary that translated the Torah into guidelines for daily living. Reading and discussing the Torah was a sacred activity and it was primarily scribes that studied, read, and taught the people. Scribes were also called rabbi, teacher, or master. Scribes were held in high esteem and, as holders of sacred knowledge for the Jewish people, their words carried a great deal of authority

These were the formal roles associated with the temple and the Torah and many of these priests and scribes belonged to one of two major religious political parties: the Sadducees and the Pharisees. The Sadducees were the conservartive party. They considered the written Torah as the final authority and rejected any oral commentary. The Sadducees were usually members of the wealthy upper class that resided in Jerusalem. They supported the political and the religious status quo. The Pharisees were the progressive party. They accepted oral commentaries of the written Torah because they were interested in applying the Law to everyday issues and to the life of the average person. This focus led to their reputation—a well-earned reputation—of being pure, pious, and holy.

By time we get to Jesus’ years on earth we know that something has gone astray because he regularly calls out the Pharisees for their hypocrisy. We even see it here in the passage in the story he tells about the two brothers. Given the way Jesus confronts and challenges the Pharisees in each gospel I suppose it is no wonder that they became the villains in the story. But here is what really struck me about the Pharisees as I read more about the religious-social-political environment of first-century Jews: the Pharisees started off with really good intentions. They had a desire for their faith to permeate through every part of their life. They didn’t want their sacred teachings to become irrelevant or sterile. They believed their entire community should be a people set apart for God, a holy people. I can relate to those intentions. Can you?

When we say “at Calvary we want more of Jesus” our intention is good, isn’t it? Doesn’t this mean that we want Jesus’ teaching and power to reach into every aspect of our life. Doesn’t this mean we want to be relevant, flourishing, and alive, growing as a community with our eyes set on God? But what happened to the Pharisees? They had good intentions and even better conduct. So why, by chapter 21, does Jesus essentially say that they are not entering the are his Kingdom people? Why not these Pharisees who faithfully studied God’s law and devoted their lives to obedience and right living?


I want to take you into the Gospel of Luke for another comparison story of the Pharisees and the tax collectors that will shed some light on repentance in the life of these two characters. Turn with me in your Bibles to Luke 18:9-14

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.”

We already know that Jesus’ treatment of tax collectors angered the Pharisees. Remember in Matthew 9, Jesus is eating at Matthew’s home with tax collectors and other disreputable sinners, and the Pharisees question “why does your teacher eat with such scum?” Tax collectors were detested by many first-century Jews because they worked for the oppressive Roman government and they often abused their authority for their own financial gain. Tax collectors were excommunicated from the temple and shunned in Jewish society. If you think of who in our society today is completely despised, excluded, or considered to be beyond redemption or forgiveness, that was the tax collector in those days.

No one liked the tax collectors but particularly the Pharisees who, by this point, were obsessed with purity; Jesus socializing and eating with such outcasts was a total affront. They hate that Jesus would welcome and befriend tax collectors. Can you imagine their reaction as Jesus tells them that it is these people that will be exalted and enter the Kingdom of God? This idea was an impossibility to the Pharisees who were doing everything they could to enter the Kingdom of God. They were confident that they were in right standing with God. 

Read again how the Pharisee prays: “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.” How many times does the Pharisee mention himself in this prayer? Four times. It is a completely self-focused and self-centered prayer. The Pharisee is displaying the epitome of what A.W. Tozer calls the “self sins”: self-righteousness, self-confidence, self-sufficiency, self-admiration. Their intentions were good and their conduct was pious, but the Pharisees put themselves at the centre of God’s story. They didn’t actually need a King in their story. The Pharisees wanted the Kingdom but not the King.


In contrast, consider at the tax collector. He stands far from others, and he won’t even lift his eyes up to heaven because he feels so unworthy. He beats his breast, over his heart, because he is so distressed over his sinfulness. The only other time we read of people beating their breasts like this is in Luke 23, in the moments right after Jesus dies on the cross. It is an expression of deep distress.

The tax collector’s intentions had been deceitful and dishonest. He is full of shame and sorrow. He calls out that prayer we studied back in Matthew 9, “God, have mercy on me, a sinner”. The tax collector puts God at the centre of his story. He needs the King in his story.


How does all this connect to your entire life being a life of repentance? Well, the first question you need to ask yourself is who is at the centre of your story? Who is in a place of authority in your life? As I mentioned early, we usually think of sin as breaking God’s command, but Jesus goes deeper than that. Sin is putting yourself in the place of God, in the place of authority over your own life.

Over the last two weeks we have explored the theme of the authority and kingship of Jesus.

Dan taught on The Triumphal Entry, showing us that Jesus is a different kind of King from any other earthly leader that has come before or after Him. The Kingship of Jesus is about His purpose, His truth, His work in the world. If you say “Jesus is King” you are acknowledging that His ways are higher than your ways.

Rusty taught last week about the authority of Jesus. He encouraged us to think of our spiritual journey as the discovery of how Jesus, the Authoritative King, is good and how our spiritual journey is discovering submission and surrender to this sovereign Authoritative King.

All these pieces go hand-in-hand to help you understand that an entire life of repentance means that you acknowledge and welcome the kingship and authority of Jesus over your life, not just in moments when you feel remorse over a sinful behaviour, but a consistent posture of submission.


Today we have looked at two different characters and their examples of repentance. Can you see yourself in their stories?

Like the Pharisees, are you keeping all the rules and aspiring to show others that you have got it all together in your behaviours? Are your intentions and conduct so righteous that it is possible that you don’t need a saviour because you are your own Saviour? Are you living life in the Kingdom without the King?

Or are you sometimes like the tax collector? Are you perhaps a bit of a mess, with intentions and actions that have gone astray? Are you beating your chest in distress, your heart heavy with shame?

We each are probably the Pharisee some days and the tax collector on other days. The beauty of the gospel is that you are not stuck in a character study. Your entire life is a life of repentance when you acknowledge your complete and utter need for the King, all the time, every moment.


To close, let me encourage you to read both Matthew 21 and Luke 18 on your own. As you read, talk with God about the following questions:

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