Day 32 (Thursday) - Matthew 27:1-10

Artwork by Ben Ober

Artwork by Ben Ober

“Repent, for the kingdom of heaven is near!” 

To recap what we talked about on Sunday, this idea of repentance - the promise that we can look at what we’re doing, realize it’s wrong, and do the opposite. We can turn around.  When Jesus said, “repent,” what he literally meant was “transform the way you think.”  

Because repentance isn’t just a change in our behaviors.  It means a change in the habitual thought patterns that caused those behaviors in the first place.  The insecurity. The doubt. The anxiety.  The pride.  The family patterns.  The fear.  The competition. The things we were taught as kids.  The shame.  The need to prove ourselves.  Repentance means a whole new brain.  It’s a whole new way of thinking and moving and being in the world, so that being the people we want to be isn’t so hard anymore.  

When we think in certain ways, our minds make literal, physical pathways.  But when we decide to replace lies and sin with truth, we're literally creating new pathways in our brains.  We are repenting and becoming new.

The Apostle Paul even went so far as to say our transformation into Christlikeness itself starts by renewing the way we think.  Repentance is part of the good news in Matthew, the overarching rubric of all of Jesus’ sermons, a promise that there’s actually a different way to live, a different way to think, a different way to be.  Repentance has power to transform our lives and the lives of those around us. God won’t always transform our circumstances, but if we let him, he will transform our minds towards them. How?  Well, “the kingdom of heaven is near,” he’d said, talking about himself.  The King had arrived with a whole new Kingdom and a whole new way of operating in the world.  We repent with in the power of the King.

Here’s what repentance doesn’t mean. It doesn’t necessarily mean that all your pain or your sin will suddenly disappear in an instant. Some of it might.  But more often than not, repentance happens slowly. Subtly. Layer by layer.  It isn’t easy. 

The great theologian, Ben Harper, wrote in a song, “You gotta fight for your mind.” Because a fight it often is, and to be honest, you might and yourself sore and bruised for awhile as you do.  And for good reason.  Like C.S. Lewis said, repentance “means unlearning all the self-conceit and self-will that we have been training ourselves into for thousands of years.”  No, it isn’t easy, and it takes a lot of practice.  

But it is a gift, and it means freedom from all the things that hold us back.  It means freedom to think about God and the world and ourselves the way God does.  

"Repent, for the Kingdom of Heaven is near!"

Matthew’s wording, then, after all this talk about repentance throughout his book, is interesting here as he describes what Judas did.  

When Judas, who had betrayed him, realized that Jesus had been condemned to die, he was filled with remorse.


It was a distinct word choice.  This word for remorse isn’t used very often in the New Testament and when it is, it is often used with intention.  The difference between remorse and repentance is a big one.  

Repentance looks forward.  It acknowledges wrong-doing, but more than that, wrong thinking, and makes an effort to change.  

Remorse looks backwards.  It says, “Whoops!  Wish I could undo that one!”  It tries to take back what happened, make amends maybe, but it makes no true change for the future.  

Repentance is a life-long process; it means making small decisions every day to think as Jesus taught us to.  It’s about being changed gradually into the people that we were intended to be.  

Remorse is about one action we wish we had done differently.

Judas felt remorse.  

Judas realized what he’d done...and he felt really, really bad about it.  He wished what he’d done, he could undo.  He tried to take it back. Maybe by dying on a tree, he was trying to make amends or giving back an eye for an eye or paying for his sins himself.  But he never allowed Jesus to change his future or to transform his mind.  

Judas had spent years walking closely with Jesus.  But he’d missed the Good News just like so many of us do.  He’d missed the forgiveness that would be offered to him that same day on the cross.  He’d missed the freedom he could have enjoyed if he’d taken his failure to God instead of trying to fix it himself.  

And he punished himself for his sin, the way so many of us do.  We berate ourselves.  We isolate ourselves.  We try to pay it back or to do enough good so that God will finally forgive us.  We numb.  We hide.  We beat ourselves up.  We beat those around us up.  We feel remorse, but so many of us will do anything we can to keep from turning around and facing the pain we caused and transforming our minds.  

You don’t have to hang yourself to miss the Good News of Jesus.

After Jesus is raised from the dead, he goes after Peter and invites him to declare three times that he will care for God’s people.  Three.   The number of times Peter betrayed Jesus.  I’d imagine these conversations did not happen without tears, without struggle, as Peter realized his own failures and turned, sometimes slowly, around.  But when Peter repents, Jesus redeems, and the most spineless failure of the New Testament becomes the backbone of the Early Church.

Because here’s the thing.  Jesus never asked us to wallow in misery, to feel really, really bad about ourselves and live with a noose tied around our necks for the rest of our lives.  

Jesus never demanded that we give him an eye for an eye, or pay him back, because no amount of beating ourselves up or paying him back can undo the damage of our sin and no amount of hard work can merit God's forgiveness.  

Jesus does not ask you to die for your sin.  He already did that.

Instead, he offers a gift: Repentance.  Transform your mind.  Live in the forgiveness that is offered to you. Receive it and forgive yourself too.  You are not condemned to death or sentenced to a life of pay-it-backs and pay-it-forwards, but released to new life, to freedom from all regrets, from all sin, from everything you’re ashamed of now and forever. 

If only Judas had waited a few hours he might have seen that they both didn’t need to die for the debt to be repaid.  Judas dies for his sins. Peter dies to them. Peter repents and lets Jesus pay the price for his sins.  Judas regrets and tries to pay for his sins himself.

And because of this, failure got the last word for Judas, but Jesus got the last word for Peter.

“Repent, for the Kingdom of heaven is near!”

Pastor Brynn Harrington


In 2 Corinthians chapter 7, Paul would one day write: For the kind of sorrow God wants us to experience leads us away from sin and results in salvation. There’s no regret for that kind of sorrow. But worldly sorrow, which lacks repentance, results in spiritual death. What kind of sorrow do you express over your sin? Does your sorrow over sin lead you towards Christ or towards yourself? Does it affect change, or are you prone to numbing or wallowing in remorse or self-pity?


Spend some time in Godly sorrow for your sins.


Think for a few minutes. What is something you can do today that is new or feels renewing.  Maybe it’s spending a little extra money for a babysitter so you can have an hour to yourself in the middle of the day.  Maybe it’s going out on the boat, eating kimchi, or taking a nap.  Maybe it’s trying a new exercise or restaurant, or having some long overdue sex with your spouse.  What can you do today that will symbolize in your own life the “renewal” and the “repentance” that comes with a life in the Kingdom? Give yourself permission to do that. 

Pastor Aaron Engler


  1. Rom. 12:2; 2 Cor. 10:5; Eph. 4:23; Phil. 2:5-8.