Repentance and Regret

The Torah teaches us that it is never too late to change.

Changing for the better is called doing teshuva. The Hebrew word teshuva, which is often translated as repentance, actually means to “return.” Return to God. Return to our pure self.

How do people become interested in self-improvement?

People have faults. The faults they have cause them to suffer in some way or another. This suffering limits an individual’s freedom and is often painful. Hence, people want to change… to improve. To be free once again.

How does one change for the better? How does one do teshuva?

There are four steps of teshuva.

-Rabbi Mordechai Rottman
“Four Steps to Change”

I know an exploration of teshuva, which is commonly translated as “repentance,” seems more appropriate to Yom Kippur than Passover, but part of the inspiration to invest more in myself along this path and at this time comes from here:

The Midrash tells us that the Jewish people had the same problem in Egypt. Only 1/5 of the Jewish people were on a high enough spiritual level to leave Egypt — and they were on the 49th level of Tuma, spiritual degradation — and were within a hair’s breadth of being destroyed.

Yet, what is amazing is that in the next 49 days they raised themselves to the spiritual level to receive the Torah at Mt. Sinai! Each day we climbed one step higher in spirituality and holiness. Many people study one of the “48 Ways to Wisdom” (Ethics of the Fathers, 6:6 — found in the back of most siddurim, Jewish prayer books) each day in the Sephirat HaOmer period between Pesach and Shavuot — which will be explained below — as a means to personal and spiritual growth. This is a propitious time for perfecting one’s character!

Rabbi Kalman Packouz
Commentary on Passover (Shabbat Chol Hamo’ed) (Exodus 13:17-15:26)

I know this is midrash and for most people, especially Christians, the above statement cannot be reasonably derived from scripture. Roll with it, OK? The midrash teaches an important spiritual lesson.

Rabbi Packouz suggests Rabbi Noah Weinberg’s 48 Ways to Wisdom (there are actually 50 of them) series as the perfect companion to accompany the days between Pesach and Shavuot for those seeking to elevate themselves spiritually.

But the first step, at least in my way of thinking, is teshuva, turning away from sin, especially habitual sin, and turning back toward God.

In Judaism, repenting of sins is more than just praying “I’m sorry” to God and maybe saying “I’m sorry” to anyone you’ve hurt. It’s a four-step process:

  1. Regret. To regret what we have done wrong.
  2. Leaving the negativity behind. To stop dwelling on the transgression in thought and action.
  3. Verbalization. To verbally state the transgression.
  4. Resolution for the future. To be determined not to let the transgression happen again.

guiltyThat might seem like only a little bit more effort than what we’ve come to expect in the Church, but that short list can be unpackaged to represent a lot of depth. I plan to take each step and explore it as fully as I can, both for my edification and yours.


What is regret and how is it different from guilt?

Well , we all know what guilt is. That uneasy queasy feeling that we have done something terribly wrong that can never be fixed…

But how is regret different?

Here is an example of regret:

An eccentric but wealthy, elderly acquaintance tells you to meet him at 2:30 pm on Sunday afternoon at Starbucks for coffee.

At 2:00 pm you are busy watching a great movie and decide not to show up to the 2:30 meeting.

That evening you find out that this elderly gentleman made the 2:30 appointment with 10 people, you being one of the 10.

Only five out of 10 arrived at the meeting. To each of the five who showed up, your eccentric acquaintance gave a bank check for $50,000 dollars.

Now you know what regret is. The feeling of missed opportunity.

When you find out that you missed out on 50 grand for a stupid movie, you feel regret, not guilt.

When we go against the will of God, the feeling we are supposed to have is regret. What a lost opportunity! We lost a piece of eternity!

When we have done wrong, whether an impulsive and momentary act of unintentional sin or repeated acts of intentional sin, it is normal and expected to feel guilty. Some people only feel guilty when they are caught or confronted about their sin, while others wear guilt around their shoulders like a bitter shroud, clinging to its fabric day and night. Rabbi Rottman describes guilt as that ”uneasy queasy feeling that we have done something terribly wrong that can never be fixed,” but the first step in repentance isn’t guilt, it’s regret.

In the example above, we see the difference between the two, but of these two experiences, guilt is much easier because, unless our soul is completely unfeeling, experiencing guilt is almost automatic.

I blame myselfGuilt is a response to doing wrong and to thinking thoughts like, “I’m a no good filthy scumbag. I can’t do anything right. God must hate me because I keep sinning. What’s the use of trying to be better when it always boomerangs on me?”

As you can see, feeling guilty doesn’t lead one to initiate change, it does just the opposite. Feeling profound guilt can be paralyzing and actually perpetuate the cycle of sin rather than change it.

We regret, as in the example above, a golden opportunity to reap great rewards. Making teshuva yields great rewards. It’s an opportunity to reconcile with the Creator of the Universe. He holds wonderful gifts for us but we have to show up at the appointment He makes with Him. Guilt keeps us hiding inside our houses, under our beds, quivering in the shadows. Regret is the feeling we have when we’ve stupidly thrown away the chance to receive free money (citing the above example) and to otherwise enrich our lives. God is a wealthy benefactor who only wants to do good for us, not to punish us for every sin we commit.

God knows we’re imperfect. God is waiting to help us. But we have to regret our sins as events that have prevented us from receiving His kindness and generosity and see that if we continue to commit those sins, we continue throwing away all of those gifts.

God is a personal God. He is aware of us. We are in His presence. He is paying attention. God is communicating to us through His world of beauty and design. He is here and available. The Almighty Creator of this whole universe is saying: My child, I love you. I created you to give you pleasure. Come, let’s explore the world together.

The Creator of the universe loves you? Wake up! That’s exciting news!

-Rabbi Noah Weinberg
“The Power of Awe”
Step Four in 48 Ways to Wisdom

Look at your life as you’ve lead it up to this point. There are such a variety of people who may read this blog that I’m sure you represent all kinds of different experiences. Some of you may be very spiritually elevated, very close to the Creator through faith in the Master. Others may be barely hanging on to faith at all because of the seeming hopelessness of your lives, because of your apparent inability to shake off sin and guilt.

Feeling guilty is the lazy way of reacting. A guilty person resigns himself to keeping his faults and does not try to take actions to improve.

Don’t use guilt feelings to justify laziness and procrastination. If a person tends to think in terms of guilt, when he hears an idea he will say to himself, “How awful it is that I’m not following that idea.”

It is more productive to keep focus on what you can do to implement the principle or concept.

-Rabbi Zelig Pliskin
“Avoid Using Guilt to Justify Inaction”
from Today’s Daily Lift #358

jewish-repentanceWe have free will to choose obedience or disobedience to God. Even when we disobey, we have free will to allow our sin to inspire guilt or regret. We have free will to select inaction or action that will lead to change. You may have sinned for years in secret or in public and feel incapable of managing giving up that sin. You may have advanced in many other areas but still fail in one or two that hold you back from a closer relationship with God. You may say to yourself that if you’ve failed in the same way for so very long, that breaking the sin habit is impossible and you are a slave to it forever.

But guilt over missing previous opportunities, if turned to regret, doesn’t have to stop you from keeping future appointments and grasping the next opportunity offered to you by God:

In each one of us there is an Egypt and a Pharaoh and a Moses and Freedom in a Promised Land. And every point in time is an opportunity for another Exodus.

Egypt is a place that chains you to who you are, constraining you from growth and change. And Pharaoh is that voice inside that mocks your gambit to escape, saying, “How could you attempt being today something you were not yesterday? Aren’t you good enough just as you are? Don’t you know who you are?”

Moses is the liberator, the infinite force deep within, an impetuous and all-powerful drive to break out from any bondage, to always transcend, to connect with that which has no bounds.

But Freedom and the Promised Land are not static elements that lie in wait. They are your own achievements which you may create at any moment, in any thing that you do, simply by breaking free from whoever you were the day before.

Last Passover you may not have yet begun to light a candle. Or some other mitzvah still waits for you to fulfill its full potential. This year, defy Pharaoh and light up your world. With unbounded light.

-Rabbi Tzvi Freeman
“The Inside Story on Passover”

Are you beginning to see why this is a good season to begin to make positive spiritual changes in your life?

You aren’t an innocent bystander in your own life, waiting on a street corner for God to drive up in a bus and offer you a ride. You don’t have to wait for God, God is waiting for you. Every time you are tempted to sin is an opportunity to keep an appointment with Him. Who knows what He has in store for you? You’ll never find out if you keep missing appointments, if you keep hiding from opportunities.

If you think I find all this easy, you’re wrong. I’m writing this in part to process my own experience and grasp the meaning of regret as a motivating force. This is only the first of four steps in the process of repenting to God. A single “I’m sorry for my sins” prayer just isn’t going to do it. Cheap grace is not sold in God’s storehouse. Salvation may be a free gift of God through grace, but you still have to show up to accept it and you need to be in a state of purity to get in the door.

purityThat state of purity, the mikvah process if you will, begins with teshuva and teshuva begins with experiencing authentic regret at having missed out on God’s blessings up until now. Seeing sin as a missed opportunity to draw nearer to God takes a lot of effort. Setting mind numbing guilt aside and allowing regret to enter your life is no easy task. If you stumble, that’s not really unexpected. But regret stumbling rather than letting it tell you some sad and sorry story about how lousy you are. Regret helps you get back up again. Guilt keeps you on the ground eating dust and ashes.

I hope to write about the second step in making teshuva soon.

The next step is Leaving Negativity Behind.


15 thoughts on “Repentance and Regret”

  1. Do you suppose that what we, especially Americans, treasure is the very thing that makes growth so difficult? Is freedom, as Paul mentioned so many times and now taken out of context, the very thing that ruins our desire for accountability? Is the freedom that we as Americans, fight so hard to keep, the very thing that drives us to individualism, thus removing the willingness to be accountable?

    It feels as though this desire for individualism, and the “mind your own business” society has driven us into a closet of sin, and as long as no one knows about it, we don’t have to be accountable for it. Even if someone knows, it is none of their business anyway.

    There was a reason James said to confess our sins to each other (James 5:16). Doing so allows us to support our fellow believers and pray for them. Doing so holds us accountable. Not with judgement or condemnation within the community, but support and encouragement.

    True growth requires coaching, accountability, mentorship, honest criticism, productive praise, and so on. As with an athlete that has born natural ability, one can only get so far playing community league baseball. To harvest that true talent takes not only real coaching, but also honest accountability. The player has to be willing to submit all weaknesses to the coach in order to get honest help.

    Public accountability would make us weird today and probably not handled with the right emotions. Repentance is hard. Especially when you’re alone and with your own thoughts. God does restore. I’ve experienced it. For me it was not immediate. I don’t know if that’s right or wrong, but it just is. It took time for me, and I still stumble and have to work again. It takes work. God seems to always show up with His tools when I ask, but I have to be willing to do the work.

    1. @Terry — Freedom is not a cause of sin — it merely removes some of the constraints that held it back. Individual privacy is not a sin — but it can be misused to conceal it. We find in Prov.25:2 — “It is the glory of God to conceal a matter, But the glory of kings is to search out a matter.” There is no sin in concealment (or “privacy”), whether done by humans or by HaShem; but “kings”, who are responsible for ensuring justice and the protection of their people, must seek to be above board and to investigate matters under their purview thoroughly. We who would be a “nation of kings and priests” (or who would emulate those called to be so) would be well-advised to do similarly, even when we fear that openness would be uncomfortable.

      Public accountability is most appropriate to public servants. Everyone is privately accountable to the One Righteous Judge whose justice is reliable. But public accountability of private individuals for private actions is tyranny unless it is voluntary. The public, even the congregation of HaShem, is not empowered or skilled to demand individual accounting unless private actions enter the public sphere; and even then it must be conditioned by methods that ensure justice and mercy — hence we see procedures such as in Mt.18. Yakov’s exhortation in Jam.5:16 is not general practice but is contextualized to deliberate individual action seeking healing. So let’s not be quick to denigrate the privileges that Americans have fought so hard to establish and maintain. They are not unbiblical, and they are not harmful if not abused.

      1. @PL – I was certainly not implying, intentionally, that the privilege we share as Americans. I am one of those that served to protect the freedom, having served 8 years, both directly and indirectly was involved in foreign deployments. I believe, deeply, the freedom we enjoy is a wonderful gift and blessing.

        My point is that having evolved into such an individualistic society, our accountability has deteriorated to the phrase, “It is no one else’s business.” While that could be true, I can not help but be reminded of the story in Joshua of Achan, who sinned in private, but affected the entire nation.

        I know this is not the exact context as my, or anyone else’s, private sin, However, don’t you think that all sin somehow creates a ripple affect?

        I was simply trying to point out that I think the lack of community support has broken down our ability to grow together. Not just in accountability for our sinful nature, but also supporting our brothers in need. Even just the openness to admit having a need is an embarrassment today because of our individual nature.

  2. I note a regrettable tendency to confuse the definition of guilt with feelings about guilt. Guilt is a state of being — it is not a feeling. Guilt is the state that results from having done something. If you did it, you are guilty; if you did not do it, you have no guilt. This may be positive or negative — one may be guilty of doing something good as certainly as doing something bad. However, one is not likely to feel guilty for doing good. It is also true that one may be declared properly as having been found not to be guilty of some specific action. This is central to the notion of justice. However, one may falsely feel guilty even if one has done nothing to justify it — but that is likely the result of the fact that all of us actually are guilty of falling short of HaShem’s expectations of us (often as a result of quite deliberate selfish choices). I don’t know how helpful it might be to recognize that another word exists in English for these negative feelings of guilt. It is the word “shame”. Nonetheless, even if we are linguistically precise, and we call a spade a spade, we call shame by its proper name, and we recognize its distinction from actual guilt, we must still face the issue you discussed above not to allow ourselves to be paralyzed by our shame. We must accept and deal with the fact of our guilt, regretting the cause of it, repenting to turn away from it, resolving to learn not to repeat it, and restoring what has been damaged by it insofar as possible. But perhaps I’m jumping ahead already to your impending discussion of t’shuvah.

  3. As the Apostle Paul said resisting sin is a matter of self control per se not like how most of Christianity perceives sin.

  4. I don’t know if American culture is the problem. I think human nature is, otherwise, the Bible would seem pretty anachronistic by now (although many out there experience the Bible that way). The Bible remains effective because it’s a record of human nature. Yes, at a certain level of detail, it describes God’s relationship with Israel, but it is relevant to all people today because at a different level, it illustrates God’s relationship with people.

    We sin. We disobey. That is our nature. In Romans 7:14-15, Paul says:

    For we know that the Law is spiritual, but I am of flesh, sold into bondage to sin. For what I am doing, I do not understand; for I am not practicing what I would like to do, but I am doing the very thing I hate.

    Until the era of the New Covenant reaches fruition, Paul’s statement also describes us. This isn’t an excuse to continue sinning, because as Paul also said in Romans 6:1-2:

    What shall we say then? Are we to continue in sin so that grace may increase? May it never be! How shall we who died to sin still live in it?

    Life is a struggle between the two “people” who live inside of us, the human being who disobeys and the person who lives in hope of Messianic days. That’s why we must pick up our cross daily, repent, and in surrendering our life, regain it through Messiah.

  5. Many cults and cult-like groups offer to solve the problem Terry mentioned. One needs to be very careful who to trust with confessing and praying.

    This is from Bill Bullock’s status today: Do not follow anyone who includes you in a statistic or who defines you by your age, your gender, your economic status, or by how your innate talents and giftings fit into his own ministry goals; follow the one who considers you unique and immensely valuable solely because of your humanity and who envisions you overcoming all obstacles, transcending all classifications and limitations, and soaring far beyond your natural characteristics, talents and giftings would ever allow you to go.

    1. @chaya — Perhaps it would not be too cynical to add to that advice: Be also at least a bit skeptical about the leader who makes you feel unique and immensely valuable, because many have been misled by a charismatic or affable personality only to find that their perception was superficial, and because even the best leaders are only humans with “feet of clay”.

      I suspect it was this awareness that induced the founders of the American experiment to insist on checks and balances to power along with public accountability of public servants.

  6. Proclaim Liberty:

    This venue, this event we call life is a learning event for all of us.

    I don’t view any of this as the “us against them”, scenario, because no two people think exactly alike anyway. The correct operating premise really has never been, “we just don’t agree”, it’s really the fact that no two people think exactly alike, we are all still learning !

    Whether it’s two Lubavitchers or two Reform Jews, or, (ie), two Baptist, even in our respective groups, no two think exactly alike, they may be 90%, on issues, but still not exactly the same.

    In so much as possible, in the time frame of history that we are in right now, “our generation”, it really is good to clearly define, and be as precise as possible about everything we talk about.

    When you talked about guilt being a state and not a feeling, that was great !

    What a great observation, but more importantly, the fact that you took the time to point that out is great.

    Our “feelings” can run totally contrary scripture, truth and fact. I woke up the other morning and told my girlfriend that I didn’t “feel” like 2+2 equals 4 anymore,, that I now “feel” like it’s really 56.

    I phoned my math professor, he treated me like General Patton talking to a coward, thank G-d he brought me back to reality !

    Thanks !

  7. Out of no disrespect or indignant supposition, I will have to disagree with this idea of guilt and regret. In my own opinion, to feel guilty is the first step to true repentance, whereas regret is prideful attempt at reconciliation. In a sense, we all regret missed opportunities because in essence we desire to be increased, respected ect, but in the spiritual sense, we regret sin as a way to justify our current actions, IE “I regret my faults because I know now they are wrong, so I will act differently.” I may take leave outside my own knowledge, but Intuitively i understand guilt to be not that i have done something that can never be fixed, but rather a profound feeling of “I owe”. In a sense, i owe a debt i can never repay. Regret on the other hand, portrays an ideology of pelagian free will, where no debt exists until the individual incurs it through action. Will we admonish original sin and free will based on our own desire to proudly claim “I know better”? Have not all sinned and fallen short? Do we not all owe a debt that we are incapable, even though we may regret our actions to bring it on ourselves, that we cannot pay? That hopeless feeling of guilt deemed improper, is actually the framework for the grace and mercy we claim, it is a debt u payable despite any regret, it is, by our efforts, something that can never be fixed. However, in repentance, we come to understand that the glory and redemption does not come through our actions, no amount of regression in logic, no point of regretful reflection will commensurate this incommensurable void that we are charged to place, in faith, to Him. Knowing that, “by grace we are save, through faith, not of ourselves, a gift of God, so that no man may boast.”

  8. Greetings, amosdway,

    I think what you’re seeing is the difference between how Judaism and Christianity classically view repentance. In Judaism that act of repentance or returning to God requires…well, acts. That is, people have to do something to repent beyond just mental ascension that they have sinned. Repentance is “operationalized” and a person has an active role in repenting and asking God for forgiveness. Forgiveness doesn’t occur until the person has completed the act of repentance which, if you continue to read the rest of my series as it is published, has a lot of “moving parts.”

    If you look at ProclaimLiberty’s comment of April 21st at 5:41, you’ll see another viewpoint on guilt as a state of being rather than an emotional experience.

    God forgives and saves through faith, but repentance is not passivity and God can’t repent for us. We have to be willing.

  9. Thank you for your response James, but I see no reason why Judaism and Christianity will have different views on repentance, the two are not separate, but rather equal parts in faith. The sacrifices and actions instilled in Judaism are the precursor to the crucifixion. Abraham was not honored by his actions with Isaac, but for his faith. Many have fallen to the faults of repentance without faith, believing their actions reap the atonement. As was the case in the Pharisees higher regard for traditions over the law. Faith is the precursor for repentance, the law being the truth of our need for atonement. Fulfilled by Christ in accordance to the law. Such is how I see a fundamental flaw lauding regretful ideology over existing guilt. Regret does motivate change, but it does not abolish the guilt, the hope in Judaism, and Christianity are not different, but rather, the same. (now I claim no enlightenment, nor great knowledge, and hopefully my grammatical errors will be overlooked, phones are not the best for typing)

    1. Scripture provides an excellent answer to the faith vs. works issue:

      What use is it, my brethren, if someone says he has faith but he has no works? Can that faith save him? If a brother or sister is without clothing and in need of daily food, and one of you says to them, “Go in peace, be warmed and be filled,” and yet you do not give them what is necessary for their body, what use is that? Even so faith, if it has no works, is dead, being by itself.

      But someone may well say, “You have faith and I have works; show me your faith without the works, and I will show you my faith by my works.” You believe that God is one. You do well; the demons also believe, and shudder. But are you willing to recognize, you foolish fellow, that faith without works is useless? Was not Abraham our father justified by works when he offered up Isaac his son on the altar? You see that faith was working with his works, and [s]as a result of the works, faith was perfected; and the Scripture was fulfilled which says, “And Abraham believed God, and it was reckoned to him as righteousness,” and he was called the friend of God. You see that a man is justified by works and not by faith alone. In the same way, was not Rahab the harlot also justified by works when she received the messengers and sent them out by another way? For just as the body without the spirit is dead, so also faith without works is dead.

      James 2:14-26 (NASB)

  10. Brother James, I by no means intended to digress into a faith and works debate, as you so clearly emphasized that it has already been laid put in scripture. However, my initial point, though I may be erroneous in my presentation, is that of challenging a use of regret to usurp guilt. We have all felt the sting of guilt, the sting of regret, and the hopelessness of allowing such to internalize themselves in our actions. Yet, I have also come to believe that in repentance, guilt is the more ideological position to uphold. I may find my view to change, with time, but I view that using regret to motivate change is an almost impious regard to the grace and mercy offered through salvation. I am not, however, urging for a dissonance from all regret. It has its proper place, but I also (and I may be young in my understanding) find nothing more contrary to hope than the prolonging reminder accompanied with regret. The ‘if I did this’ or ‘if I did not do this’ reflections of regret do not (in my opinion) bolster a turning away as required by repentance. But in the conviction of my guilt, I can understand that I have a price to be paid, a debt to be owed, a fault I can not, by my efforts, repair, and a burdon placed on me by the law that I can not remove. This is the point of salvation, the rolling away of the stone, when the guilt is removed, and after, comes the need for works. Not that salvation may be earned, not that you must constantly attend to its upkeep, but out of gratitude and reverence for the great price paid on ones behalf, and so that others may be made aware of the gift and freedom in Christ. In a sense, if repentance is motivated by regret, rather than thankful humility, it becomes a self-righteous imprisonment. That is why (in my limited understanding) I find the guilt of my actions, a more repentant motivator for change. For in knowing I have done something I cannot rectify through any works, the grace and mercy offered through forgiveness, becomes the true hope in faith.

    1. I suppose it comes down to the difference between how Christianity fundamentally views sin and repentance and how those concepts are views classically in Judaism. In some sense, both Christianity and Judaism have different (but overlapping) ways of conceptualizing an encounter with God. I’m not going to preach a right or wrong to it, and endlessly debating whether guilt or regret (or some combination of the two) is the better “tool” by which to begin a journey of repentance is probably not useful. What I’m doing with this series (and part two will publish on my blog in a little over an hour as I write this) is attempting to look at repentance from a different perspective than one we normally apprehend in the Church. My understanding of repentance as it has been explained to me by other Christians or as I’ve seen it practiced by some other Christians, is that it’s an all too quick and “easy” affair, involving a simple prayer of “I’m sorry, Lord” without much of anything else attached.

      Now that may not represent how Christian theologians understand repentance, but I think that many Christians in the pews imagine repentance to be a far less complex affair than it really is, that is, if the Christian it truly repenting. What I’m attempting to do here in this brief review of the Jewish concept of teshuva, is to draw attention to repentance as a far richer and more dynamic experience than what many Christians my imagine. I’m trying to get people to think, re-evaluate, and hopefully, take repentance a bit more seriously. It’s apparent that you do already.

      Personally, I find an encounter with God as an opportunity to get closer to Him and to allow Him to teach me to be more like the person He designed me to be. I’m sure I’ve missed many opportunities in the past and, being a flawed human being, that I’ll miss certain opportunities as they are yet to occur. Sin inhibits encounters with God. In your paradigm (as I understand it), a person must feel guilt and shame as prime motivators for initiating an act of repentance. From a more Jewish perspective, the initial motivator is the realization that so much time, energy, and resources have been wasted in temporal sin, costing the person their relationship with God and the eternal benefits of living a life of holiness. I can distill both experiences into the statement of a person coming to the understanding that they have sinned and saying to themselves, “How could I have been so stupid. This has to stop. I need to go back to God,” and then turning to God in humility and contrition asking for the strength to come back home.

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