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There are certain sins, habits, and issues in my life where I’ve struggled to truly repent. I’ve prayed, promised to do better next time, memorized Scripture … only to fall again. However, there are other sins and sinful patterns that are not issues in my life and others still where repentance is quick and enduring. I’m asking why do some sins tend to linger longer and the struggle to stop them is much harder?

For sure we are prone to some sins and their associated patterns due to our particular personalities and even our family histories. Godly wisdom and training in godliness (I Timothy 4:7) are necessary to put these sins “to death” (Romans 8:13). But I’m specifically thinking of sins where we’ve done all we know to do, all our teachers, pastors, and mentors tell us regarding fighting the flesh … and yet the sin and its power over us seemingly remain undefeated and undeterred. These sins have sometimes been called “besetting sins” because of their relentless and persistent assault on our Christian walk.

Here are three questions that might open us to new grace for greater victory over these relentless sins.

Am I experiencing true grief for my sin?
We can easily make confession of sin a mere ritual that does not affect or come from our heart. For repentance to be real and lasting, it must come from brokenness. Not the brokenness of embarrassment or shame from sin; not the brokenness caused by the consequences of sin; and not the brokenness of failure—as in failing in our performance. God wants us to be broken because we have grieved and hurt Him. Puritan Preacher Thomas Watson called this “holy agony.” Without this, repentance has not occurred, and the besetting sin remains.

You do not want a sacrifice, or I would give it; you are not pleased with a burnt offering.
The sacrifice pleasing to God is a broken spirit. You will not despise a broken and humbled heart, God.
Psalm 51:16-17 [CSB]

Do I really hate my sin?
We should hate the sin because of how it affects God and how it affects our capacity to know, sense, and relate to God. Our goal is purity and holiness, not compromise, not doing better, not having a good day and not sinning less often. We remember Jesus’ word that “Blessed are the pure in heart for they shall see God” (Matthew 5:8, NASB).
As we progressively come to prize and love Christ more correctly and completely, we will hate our sin. Without hatred of sin, the possibility of negotiating with it remains.
Watson’s words are again helpful: “Sound repentance begins in the love of God and ends in the hatred of sin … Christ never loved till sin is loathed.”

Then you will remember your evil ways and wicked deeds, and you will loathe yourselves for your sins and detestable practices.
Ezekiel 36:31 [NIV]

Have I prayed for God to give me true repentance over my particular sin?
Like everything in following Christ, we must realize that apart from God we can do nothing (John 15:5). Therefore, in prayer, we ask for a heart of repentance, for love for Christ to grow, and for hatred of our besetting sin to increase.
This lesson is important because we can easily drift into the futile cycle of trying to defeat sin through self-effort and trying harder. This is a guaranteed path to frustration and even loss of faith, but we must realize that we are not walking by faith in the first place when we fight sin this way.

Paul said that sin is put to death “by the Spirit” (Romans 8:13) … not by our strength and power. Practically, this means God is likely to give us a promise from the Word His Spirit inspired to trust, search us at deeper levels to uncover pride and woundedness, and perhaps teach us a spiritual discipline to practice as a means of more grace. We must accept and depend on what the Lord gives and apply it strenuously in the fight of faith … victory is ours in Christ!