top of page

The Art of Repentance


Douglas A. Wheeler, ThD, PhD

            There seems to be something quite prevalent in the Body of Christ today. That something is called guilt. This is not the kind of guilt that a person feels when they have committed a sin or made a mistake. The kind of guilt that is being referred to here is the guilt that seems to hang on long after one has repented from their sin. This is the kind of guilt and shame that seems to just “keep on giving.” This is an unhealthy type of guilt. If you have never experienced this phenomenon, then you probably should not read any further, but drop to your knees and thank the Lord that you have never experienced anything as gut-wrenching as this. This type of shame, this type of guilt, over past mistakes and failures somehow never seems to go away but becomes a never-ending agony.


            You have probably had others tell you that all that is necessary to be free from this type of guilt is to ask the Lord for His forgiveness, accept it, and trust it. But what if you tried that and it does not work for you? Does this mean that you have no faith? Does this mean that you do not believe that the Word of God is true for you? Have you ever wondered if you have “quenched the Holy Spirit of promise?” Worse yet, does this mean that you have committed blasphemy of the Holy Spirit?


            We, as believers, should be concerned with living pure lives before the Lord. We should be concerned about sin. However, it is not realistic to think that life can be lived totally free from mistakes and failures. The fact of the matter is that Christians do sin. In our minds we know that when we sin we have an advocate with the Father. We know that if we confess our sins, He is faithful and just to forgive us of our sins and to cleanse us from all unrighteousness. But what about this guilt? 


            The person of concern is the believer who genuinely loves the Lord, but who, after asking forgiveness for a sin, still cannot receive the assurance of that forgiveness. Maybe rather than continually focusing on the sin, we should focus on repentance. Is there more to repentance than simply saying that you’re sorry? Is there more to this than just turning around and going a different direction? If not, why do so many Christians feel that they must “work” their way back into the good graces of the Lord after an act of sin has been committed? Why are we not taught as much about repentance as we are about sin? Maybe if we were taught more about repentance we would not be quite so ready to be involved in sin. What is there in our Hebraic roots that can teach us about repentance?


            In order to answer these questions we need to take a good look at not only sin but also at repentance. First of all, we all commit acts of sin. Each one of us like sheep have gone astray and each one of us have, at one time or another, turned to our own way. It is not possible for a believer to go through this life and not “mess up” at one time or another. The question is not whether we will sin, but what we will do after we have sinned. Do we ask forgiveness and run back to the church to do some “good works?” Do we blame our actions on the devil and refuse to be a part of our own “freedom?” Do we continue to focus on what we have done wrong rather than spending a little time looking at what we have done right? Worse yet, do we see the sin in the lives of others but refuse to see it in our own? Do we really need repentance?


            This whole idea of repentance was brought to the forefront of my own life in a situation concerning my teenage son. In the town where I live, the driveways are in the rear of the house and not out in front. This means that to park the car in the driveway, we must approach our house through the alley. That is really no problem since the alleys are paved and easily accessible. One day my teenage son was coming home and I happened to be in the yard as he drove down the alley. He must have been driving about 50 miles per hour down the alley. This is an extremely dangerous thing to do as most of the yards have fences, and it is not possible to see when someone is backing out of their driveway. It would also be difficult to see a child walking out of his driveway to get to the alley, not to mention the problem with all of the dogs that casually wander in and out of driveways in the neighborhood. When he pulled up into the driveway and got out of his pickup, I said to him in a not-too-quiet voice, “What are you doing driving down the alley that fast? You’re going to kill yourself or someone else.” He looked at me like a light came on in his brain and said, “You’re right, I just did not think. I am sorry, Dad.” Did I forgive him? Yes. Did he repent? Maybe. Was repentance complete? No way! You see, he asked for forgiveness for his mistake and that forgiveness was given, but repentance was not complete. There had to be a conversation about his actions so that he could evaluate not only what he had done, but the dangers associated with that action. He had to understand the possible consequences in what he had done, not only to himself but also to other people. Likewise, we need conversation with the Lord when we sin. We need to do some evaluating on why we did what we did. 


            The Jews before and around the time of Jesus understood this facet of repentance. They had a system of evaluation in place called the “Prerequisites of Repentance.”1 We know that because of the atoning sacrifice of Jesus, there is no prerequisite of repentance, that forgiveness for sins is instantly given. However, if we would consider this “art of repentance,” we might find that we would not suffer from “hang-on guilt.” We would also find that we would not spend as much time wondering about whether or not we are forgiven, and we certainly would not try to “buy our repentance with our good works.” Let’s consider this “art of repentance.” 


            Early believers looked at repentance as a return to “life.” They viewed life as abudah--complete and not broken down into compartments. This term is from the root בדד and it means, to disjoin, to divide, to separate. There is contained the idea of cutting or tearing apart, and hence dividing.2 God was not only the beginning of all life but disobedience to Him resulted in a diminished quality and fragmented form of life. For life to be lived in fullness there must be recognition that everything in life proceeds from God. He is the head of all that is life. This means simply that they did not live their life one way in the secular world and a different way in the church. They lived all life under the authority of God. There was a recognition that even something as simple as tying a shoe was a spiritual act because it was God that gave them the ability to breathe air and muscles to bend down and tie that shoe.


               Consider this idea of abudah another way. The Rabbis taught that life means “divine essence in physical reality, and our ability to transcend the limitations of physical existence. Therefore, when we do or think or dwell on something, if this is not dedicated to our service to God, if this is not done with our intention of bringing down godliness, then it is not done for the purpose of sanctifying God. And those moments that we so live are dead moments for us. They do not encompass eternity…. That is the reason that David said, 'I have set the Lord always before me.' But when we forget God and we do not set God before us, we lead ourselves into sin.”3 Abudah then is the recognition that the Lord is our head, our leader, and our guide, and we are His servants. We are also His worshippers. 


            Sin interrupts abudah. When a person sins, he or she must repent in order to keep the face-to-face relationship with the Lord intact. In Hebrew, one word for repent is נחם (nacham) which means, “to draw breath, to grieve, and to lament.”4 This word gives us the idea that sin causes us to draw breath like a sigh, to grieve over our actions and to lament. This word can also mean to comfort. Does this mean that the Holy Spirit will comfort us as we turn from our sin, come back to Him, and are truly sorry for our actions? Is this all there is to repentance? Do we only grieve a little, groan a little, turn around, run back to the Lord and say I am sorry? Is this even a fair question in light of the fact that the average person runs away from the Lord after committing sin rather than running toward Him? Let's postpone the answers to these questions and consider repentance from a different light.


            There is another Hebrew word that expresses or defines repentance and that is תשובה (teshuva). This word expresses the “essence of repentance.” Teshuva begins to explain that there is more to repentance than simply saying I am sorry. There are other questions that should be asked when a person sins that go beyond just forgiveness. One of these questions is: What have you learned as a result of your actions or of your sin? The Lord does forgive us immediately when we ask Him to. I John 1:8-9 says, “If we say that we have no sin, we deceive ourselves, and the truth is not in us. If we confess our sins, he is faithful and just to forgive us our sins and to cleanse us from all unrighteousness.”


            Let’s go beyond the point of forgiveness to the point of learning. This is what is meant by this idea of the "essence of repentance." Jewish believers in the first century knew that this word for repentance תשובה (teshuva) formed an acronym for a deeper idea of repentance than just being forgiven. To them, it was just as much a question of learning as it was of forgiveness. It was a question of returning to abudah and returning to the very source of all life. It was a question of how they could live in deeper intimacy (yadah) with Him. It was the visible demonstration of their willingness to be obedient to His authority and leadership. The acronym for teshuva is made up of five different passages of Scripture. Each passage of Scripture begins with each of the corresponding letters of the word תשובה


ת:                תָּמִ֣ים תִּֽהְיֶ֔ה עִ֖ם יְהוָ֥ה אֱלֹהֶֽיךָ      (Deuteronomy 18:13)


ש:                     שִׁוִּ֬יתִי יְהוָ֣ה לְנֶגְדִּ֣י תָמִ֑יד       (Psalm 16:8)


ן:                                    וְהָלַכְתָּ֖ בִּדְרָכָֽיו         (Deuteronomy 28:9)


ב:                                בְּכָל־דְּרָכֶ֥יךָ דָעֵ֑הוּ         (Proverbs 3:6)


ה:                        הַצְנֵ֥עַ לֶ֖כֶת עִם־אֱלֹהֶֽיךָ        (Micah 6:8)



     Therefore, by taking the first letter of each verse of Scripture, in Hebrew, we form the word for repentance תשןבה. Following this pattern, there are then five principles that we should learn during repentance. This does not mean that you must work for forgiveness. After committing a sin, however, a person should examine his/her behavior or the choices made in light of these five principles (concepts) to see where or why abudah has been breached. We can state this another way. When we break one of these principles or concepts it weakens our relationship with the Lord. To see this clearly, we must examine these five concepts or principles.


            ת. Deuteronomy 18: 13, “Thou shalt be perfect with the Lord your God.” This concept has to do with the idea of being perfect. This word does not mean, “without error.” The word translated perfect in Hebrew is תמים from the root תמם (tamam), and it means, “ to be complete, whole, sound, upright in conduct, blameless. It also means to be finished.”5 It is in the person of Jesus through our relationship with Him that we can be complete, whole, and sound. It is only through the interaction of the Holy Spirit on our lives that we can be upright in our conduct. Likewise, it is only through accepting the atoning sacrifice of Jesus that we will ever be blameless. Paul said it this way: “For in Him we live, and move, and have our being: as certain also of your own poets have said, for we are also his offspring.”


     The starting point of abudah is accepting the sacrifice of Jesus and His atoning work on the cross. It is accepting His leadership in our life. It is dying to self and becoming a worshipper and servant for the Lord, which is the primary idea of abudah. He is the author and finisher of our faith. The concept that is expressed here is that we are to follow the leading of the Lord even when we do not understand it and even when we question it. His ways are not our ways and we are to follow His ways and not our own. Sin is following our own way and becoming our own leader. When we sin and repent, we need to examine our behavior to see where, when, and why we went down our “own road.” Either the Lord is running your life or you are. Part of examining ourselves in repentance is to honestly accept who is really in control of our life.


            ש.  Psalm 16:8, “I have set the Lord always before me: because he is at my right hand, I shall not be moved.” In the first part of the verse there are two very significant words. These words are “set” and “before.” Let’s begin with the word that is translated “before.” In Hebrew this is the word נגד (neged) and it means, “to be in the front part of, in the presence of.”6 This is speaking of a face-to-face relationship with the Lord. It is a relationship that is eye-to-eye, nose-to-nose, mouth-to-mouth. The word translated “set” is the Hebrew word שוה (shavah) and it means, “to set, to place, to be level, to be even.”7 This means to allow the Lord to bring you into an intimate face-to-face relationship with Him, which will make you level and even. In other words, your relationship with the Lord has the ability to bring you to a place of balance. Sin will interrupt the face-to-face relationship that you have with Him and interrupt your balance. When the law was given to "have no other gods before Me," we see this very idea. Do not let anything be exalted to the level in your life that would come between or break this face-to-face relationship. When we sin and ask for forgiveness, God will indeed forgive us and bring us back into this face-to-face relationship. However, it is the second part of the verse that gives us the area of evaluation. David said, “Because he is at my right hand, I shall not be moved.” This is speaking of position of authority. In order to properly maintain a face-to-face relationship with the Lord, He must be in the position of authority in our life. If we want stability (not being moved) we must allow Him to accept the responsibility and authority of our life. When we sin, we have assumed the authority of our life. We have become face-to-face with ourselves. We need to evaluate our actions to see how self became exalted to the position of authority. His will for our life must be preeminent.


            ו.  Deuteronomy 28:9, “The Lord shall establish thee an holy people unto himself, as he hath sworn unto thee, if thou shalt keep the commandments of the Lord thy God, and walk in his ways.” We are a holy people. We are קדוש (qadosh) clean, set apart for the work and use of God. We are to walk (׳לך) in His ways. What are His ways? We are to walk with His attributes. His attributes are the fruit of the Spirit. Paul says that “the fruit of the Spirit is love, joy, peace, longsuffering, gentleness, goodness, faith, meekness, temperance: against such there is no law. And they that are Christ’s have crucified the flesh with the affections and lusts. If we live in the Spirit, let us walk in the Spirit. Let us not be desirous of vain glory, provoking one another, envying one another.” When we sin, we are not walking in the Spirit. We are not walking in the attributes of God. We need to evaluate our actions and thoughts to see if they line up with the fruit of the Spirit. If they do not, we must make some adjustments. We should not be content with short-term change (behavior modification) but long-term, heart and life change that only the Spirit of God can bring.


           ב. Proverbs 3:6, “In all thy ways acknowledge him, and he shall direct thy paths.” The word translated “acknowledge” is the Hebrew word ׳דע (yadah). This word means to get to know, to become familiar with and to become intimate. It means to touch and handle with the hands. It is the same word used when the Scriptures said that Adam knew his wife Eve and she conceived and gave birth to Cain. This is a word of deep intimacy. In all of our ways, our goings, our deeds, our thoughts, our actions, we should be intimate with the Lord. There is another important aspect to this word. To be intimate with someone to this level, there must be the assuming of responsibility. When we read that Abraham knew Sarah his wife, it is speaking of something much deeper than just physical intimacy. He assumed the responsibility for her life. It is the same for you if you are married. You assumed the responsibility for your wife when you married her. Without sounding too simplistic, you assumed the responsibility of providing for her needs, both physical and emotional, as well as helping her achieve her goals and dreams. If order for that to take place, she had to allow you to assume the responsibility for her life. We are to walk in an intimate relationship with the Lord. We should see Him or be aware of His presence in all that we think or do. He wants to assume the responsibility for our lives. We must allow Him to. We see this very idea in Matthew 7:21-23, “Not every one that saith unto me, Lord, Lord, shall enter into the kingdom of heaven: but he that doeth the will of my Father which is in heaven. Many will say to me in that day, Lord, Lord, have we not prophesied in thy name: and in thy name done many wonderful works? And then will I profess unto them, I never knew you: depart from me, ye that work iniquity.” What is being said here? Is Jesus saying that they were workers of iniquity because they were not intimate with him? Is He saying something much deeper still? Is He saying that they had never let Him assume the responsibility of their lives? When we sin, we take control. Our life is indeed a question of control. Either God is controlling our lives or we are. If we are in control then we have in essence become our own God. When we sin, we need to not only ask forgiveness, but invite the Lord in to take over absolute control of our life.


            ה.  Micah 6:8, “He hath shewed thee, o man, what is good; and what doeth the Lord require of thee, but to do justly, and to love mercy, and to walk humbly with thy God. The word translated “humbly” here is the Hebrew word צנע (tzana) and it means, “to be submissive and modest.”8 We are to live our lives in submission to the Lord. When we repent from our sin and mistakes we need to evaluate ourselves to see if we are really walking in submission to Him and to His will for our lives.


          These five concepts form what we can call the art of repentance. These are not intended to become “works” but points of examination for your life. If you sin, you know that you have an advocate with the Father, and He is faithful and just to not only forgive you of your sin but to cleanse you from all unrighteousness. These concepts are not intended to help you work your way back to God but can become points of learning and consistent change. These concepts will aid you in continually walking with the Lord in a face-to-face relationship. Evaluating your actions and thoughts by these five concepts, you will be less likely to sin. If you do, evaluating your life in terms of them can and will bring lasting change into your life. You can learn from your mistakes and your sin and not live in regret and guilt over them. You will not suffer from “hang-on guilt.” You will find that your relationship with the Lord takes on a new dimension of not only service, but also worship. Something good can indeed come from bad. You will not wonder where you stand with the Lord, but will be a part of an ever-deepening, ever-growing relationship with Him. Next time you make a mistake or commit a sin and you ask for forgiveness, take a few moments to examine your actions in light of תשובה. They are grouped together here for your prayerful convenience.


            ת.  Deuteronomy 18:13—Are you following the leading of the Lord even when you do not understand what He is doing?


            ש.  Psalm 16:8—Are you walking in a face-to-face relationship with the Lord, or has something interrupted it and become more important? Is Jesus the authority in your life?


             ו.  Deuteronomy 28:9—Are you walking in His ways? Are you walking in the fruit of the Spirit?


            ב.  Proverbs 3:6—Are you bringing the Lord into everything you do? Are you allowing Him to fully assume the responsibility for your life?


             ה.  Micah 6:8—Are you in submission to the Lord Jesus Christ?


Peace be unto you!





1 Note: The acronym of תשובה was taken from Building Blocks of the Soul, Matityahu Glazerson, Jason Aronson, Inc., New Jersey, 1997, pg. 310.


2 Gesenius’ Hebrew-Chaldee Lexicon to the Old Testament, Wm. B. Eerdmans Publishing Co., Grand Rapids, Michigan. June, 1978, pg.103.


3 Haralick, Robert, The Inner Meaning of the Hebrew Letters, Jason Aronson, Inc., New Jersey, 1995. Pp.115 and 121.


4 Gesenius, pg. 544


5 Ibid. pg. 867


6 Ibid. pg. 530


7 Ibid. pg. 809


8 Ibid. pg. 713

















bottom of page