What Does Repenting Feel Like?

A worldly ship headed east, powered by the prevailing winds. Ports of destination were lewd entertainment, coarse language, excess in food and drink, a life of forgetting God, coveting what belongs to neighbor and living for self.

Eventually, this party boat will fall off the edge of the world into never ending flames of judgment but of course no one on board wants to talk about that. Hell bent and hell bound, it’s master and commander, the unbeliever – says each day: “Hoist the sails, full speed ahead.”

Then a strange wind begins to blow and a powerful storm, like a giant hand, suddenly turns the ship around to travel in a whole new direction! You immediately throw some cargo overboard to make room for new valuables. There is now a new Commander, on a new course with a new destination, because an unpredictable wind turned the ship around.

Now there are new ports of paradise, like humility, love of God and neighbor and a life of self-denial, repentance and faith, all for God’s glory.

This parable illustrates that repentance is fundamentally a change of direction and therefore destination and therefore essential if anyone is to go to heaven. Occasionally, some graffiti is true. “Turn or Burn” comes to mind.

Repentance is a definite change of heart and mind that leads to a turning from sins to the Savior in a sincere commitment to forsake sin and obey King Jesus. The call to repent is urgent, unequivocally part of the gospel message and therefore part of every true conversion experience. Repentance is not a P.S. to the letter from God about the gospel. It’s not an optional rider to your fire insurance policy.

Repentance results in forgiveness, eternal life, a saving knowledge of the truth and salvation. God Himself is the ultimate source of repentance as He pours out the Spirit of grace upon us and we become willing and able to turn from the known sins in our lives.

But what does it feel like to repent? Before I had ever kissed a girl, I wondered what it would feel like? Don’t laugh, so did you. Now, let me assure you if you haven’t or forgotten, this is not what repentance feels like. I suppose it is more like giving birth – an intense pain for a greater gain.

Recently someone in our church gave birth to a 9 pound, 9 ounce baby boy, all natural. Her husband commented on the birth, “I didn’t know she was capable of screaming like that – it was like a war cry from Braveheart.”

And because it hurts, it will eventually and sometimes immediately involve strong negative emotions. As Puritan pastor Thomas Watson wrote, “ the sorrow for sin is not superficial: it is a holy agony.”

Faith has everything to do with claiming Christ and the promises of God in the gospel.
Repentance has everything to do with turning from sin and avoiding God’s judgment. So where faith results in joy over holiness and finding the treasure of Christ, repentance results in grief over our unrighteousness and inward pain of not pleasing God.

Faith is the eye of faith looking to Christ. Repentance is the tears running down your cheeks.

In the Bible, repentance is associated with some strong negative emotions. The first is the feeling of loss or mourning. In Biblical times, they demonstrated repentance in “in dust and ashes” or “sackcloth and ashes”, as visible, tangible, outward reminders of mourning over sin. It was like water baptism – an outward sign of an inward reality.

In Job 38 – 41, we find the most thorough dressing down anywhere as God drills Job with some 68 questions that Job can’t answer. After a while, Job tries to respond: “Behold, I am insignificant; what can I reply to You? I lay my hand on my mouth” (40:4). Yet God was not finished. When He is, Job is undone and says, “Therefore I retract (recant, take it all back), and I repent in dust and ashes” (42:6). In signs of humility and brokenness and grief, Job takes on the posture of a mourner.

Since all mourning is related to loss, the question becomes, what does repenting have to do with loss? First is the loss of a once cherished sin. At some level, there is the grief in giving up the parties, sexual immorality, the drink, the idols of your unbelieving life. There is the pain of parting with old friends who reject Christ. Sin was fun and pleasurable for a season.

But even more significant is the mourning the loss of fellowship w/ God brought on by sin. At conversion, this mourning sees the wasted life, loss of time and money and years of living in vanity and pride. Once convicted and converted, you grieve over how you have lived before a holy God, the waste and shame of it all.

As a believer who practices ongoing repentance, we grieve over displeasing God, misrepresenting God and missing opportunities to love and serve others. Especially for believers, true repentance sees sin as that which causes the greatest loss possible (fellowship with God) and therefore some of the deepest grief. It is really to our everlasting shame that we don’t mourn our sin more than we do.

Every sin is against our neighbor in some way. Every sin is against our own souls and lives and robs us of joy. But infinitely worst of all, every sin is against God. To not mourn our sin just reveals how little we really value God.

Our sorrow for sin must surpass our worldly sorrow. We cry over lost people, broken bodies, lost investments, and shattered dreams, but how often over our sin? We lose fellowship with God and say to our shriveled up souls, “oh, it’s ok, here, watch another movie. Take in another ball game. Here, this favorite distraction will take His place.”

What brings greater pain and loss than sin? How we cry and whine over our bodies and care so little for our souls! We don’t mourn sin as we ought because we don’t value fellowship with God as we ought.

We rarely grieve the interruption of infinite value but frequently grieve the loss of earthly value. How upside down we are. We are sadder over our team losing the big game than when we break fellowship with God. We are sadder over the stock market drop than the drop of our souls into sin. Jesus was trying to help us. “Blessed (truly happy) are those who mourn, for they shall be comforted.”