October 2, 2022|ז' תשרי ה' אלפים תשפ"ג Shabbat Shuva Drasha: The Power of Regret By Rabbi Jonathan Muskat

French entertainer Edith Piaf, jazz legend Ella Fitzgerald, British pop star Robbie Williams, Cajun band Steve Riley and the Mamou Playboys, American bluesman Tom Rush, Country Music Hall of Fame inductee Emmylou Harris and rapper Eminem have something in common. Each of these artists have recorded a song entitled, “No Regrets.” This credo, this belief system, of no regrets is so popular in today’s society as we have swept this emotion under the rug.

In his book, “The Power of Regret,” (p. 7-8), Daniel H. Pink writes:

““I don’t believe in regrets,” says Angelina Jolie. “I don’t believe in regrets,” says Bob Dylan. “I don’t believe in regrets,” says John Travolta. And transgender star Laverne Cox. And fire-coal-walking motivation maestro Tony Robbins. And headbanging Guns N’ Roses guitarist Slash. And, I’d bet, roughly half the volumes in the self-help section of your local book store. The U.S. Library of Congress contains more than fifty books in its collection with the title No Regrets.

Embedded in songs, emblazoned on skin, and embraced by sages, the anti-regret philosophy is so self-evidently true that it’s more often asserted than argued. Why invite pain when we can avoid it? Why summon rain clouds when we can bathe in the sunny rays of positivity? Why rue what we did yesterday when we can dream of the limitless possibilities of tomorrow?”

A no regret philosophy is understandable. After all, feelings of regret are viewed as useless and unproductive. Additionally, they can become so paralyzing. Moreover, it is human nature to revisit the past and invent alternative narratives, fictional storylines that never existed. How many of us obsess about a seemingly bad choice that we made, about what we should have done and what we could have done. If we finish second in a race or a competition, we obsess over the possibilities, like if only I would have trained harder. These thoughts often lead to anxiety and even depression. On the flip side, can negative emotions like regret stimulate human growth in some circumstances? What is the Torah’s perspective of regret? Does the Torah believe that there is value to regret and if so, when does regret propel us forward and when does it paralyze us? That is the question that I would like for us to study today.

Some of us tend to associate the emotion of regret as being one stage in the process of teshuva, or repentance. The truth is that if you go through the Torah’s discussion of teshuva, there is no mention of regret. The Torah speaks about viduy, confessing one’s sin, in Parshat Nasso (5:7), and the Torah speaks about teshuva, or returning, to God, in Parshat Nitzavim (30:1, 2). There is no indication of how we return to God. Maybe it doesn’t matter. Maybe the point is simply that we confess our sins. We admit that we disobeyed God and then we return to God and observe His mitzvot and the method is unimportant.

However, in the navi we find language relating to the steps of repentance. Sefer Yeshayahu describes leaving the path of sin (55:7). Sefer Yirmiyahu speaks of “nechama,” (31:17) which Rashi and the Radak explain as regret and the Radak explicitly states that our teshuva is incomplete without regret and he uses Sefer Yonah as a prooftext that associates the word “nichamti” with regret.

Now the Rambam in two places in Hilchot Teshuva writes about the element of regret. In Perek aleph (1:1), he writes that confession, whose source is in Parshat Nasso, includes saying that I sinned and I regret and embarrassed of my sin and I will not return to my sin. In Perek bet (2:2), he writes that repentance includes leaving the sin, committing never to sin again and he cites the pasuk from Yeshayahu, and it includes regretting the sin and he cites the pasuk from Yirmiyahu, and then he must verbalize all of these ideas as viduy. Regret clearly is part of the teshuva process according to the Rambam. It seems as if in the Chamisha Chumshei Torah, the Torah states the action of teshuva which is the confession and the navi then speaks of the inner experience of teshuva which is codified in the Rambam. Certainly, though, the Torah believes that negative emotions like regret have a place in our lives. Regret can help us learn, grow and achieve our full potential. No regret means no reflection which means no growth.

Does that mean that the Torah rejects the “no regrets” philosophy completely? Does the Torah believe that we always view regret as a constructive emotion, an emotion that we should always embrace? Is the Torah not concerned about being obsessed over the past and anxious over the past and depressed over the past?

Let us learn a gemara in Masechet Taanit. There the gemara states (16a) that if I confess but am not “chozer bah,” perhaps meaning that I do not repent for the sin, then it is similar to immersing myself in a mikvah to purify myself while I am holding in my hand a dead creeping animal which makes you tamei. What does the gemara mean when it states that I confess without repenting? Rashi explains the gemara to refer to a situation where I have stolen an object and I confess my sin without returning the stolen object. As such, his explanation is not relevant to our question. However, the Rambam (Hilchot Teshuva 2:3) understands the gemara to mean that anyone who confesses his sin without committing to not to sin again is similar to immersing with a dead creeping animal in my hand. The Rambam cites the pasuk in Mishlei (28:13) that only a commitment not to sin again is a sign of true regret.

In his Sefer Shaarei Teshuva (1:11), Rabbenu Yonah makes a similar comment when he compares regret, confession and prayer to immersing in a mikvah, and a commitment not to sin again in the future to throwing away the sheretz, the creepy dead animal, and he cites the pasuk in Yeshayahu regarding the element of commitment not to sin in the future.

Both the Rambam and Rabbenu Yona express the Torah’s nuanced position regarding regret, that regret is insufficient without a strategic plan to change. Regret alone is unproductive. It may not be helpful and it may be harmful in many situations because it could lead to paralysis, anxiety and depression. However, when it’s combined with a plan, a commitment for the future, then it’s valuable.

Rabbenu Yona actually distinguishes between two different types of scenarios. If someone sins occasionally when his desire gets the best of him, first he should regret over having let his desire get the best of him and then commit not to sin again. However, if someone repeats his sin and is going down a bad path, then regret alone doesn’t work without a plan first. You can feel bad all you want if you find yourself in a bad place spiritually or emotionally, but the first thing you need to do is to extricate yourself from the path of sin and commit yourself to remain removed from that path. Once you do that and you have a clear head and you find yourself in a better place, then you can pray to God and then you can express remorse. Expressing remorse while still being mired in a sin accomplishes nothing.

This approach sounds a lot like stimulus control theory, that sometimes it’s not our intentions which control our behaviors but it’s the effect of stimulus on our behavior. Often if we change our environment, then we can more easily change our behavior. For example, instead of feeling bad for yourselves that you may not exercise enough, you resolve to pack your gym clothes in a bag the night before and place them right next to your door so you will make sure that you will go to the gym the next day. Or if you are addicted to alcohol, resolving not to have any alcohol in your house is far more effective than simply expressing remorse over your alcohol addiction. Or if you have trouble davening or going to minyan in the morning and you resolve not to check your emails or WhatsApps or Facebook until after you finished davening. Regret sometimes is not the first step. The first step when you have really bad habits or are in a bad place is to resolve to change those habits, extricate yourself from the bad situation before expressing meaningful regret.

At this point, we seem to have the answer. Regret by itself is bad. Regret combined with a plan for the future is good. But it’s not so simple, because I want to take a deeper dive into the Rambam’s understanding of the role of regret and the commitment not to sin again. The Rambam seems to be inconsistent and how we deal with this inconsistency is crucial in how we should approach Yom Kippur.

Here's the inconsistency. In Chapter one of Hilchot Teshuva, the Rambam writes that our teshuva is first regret followed by a commitment not to sin again. However, in chapter two the Rambam writes that teshuva is first a commitment not to sin again followed by regret. So what is the proper order? Or does the order not matter?

Rav Soloveitchik (“On Repentance,” p. 200-201), explains that the Rambam writes about two different reactions to sin. In chapter one, he writes about an emotional reaction to sin and in chapter two, he writes about an intellectual reaction to sin. Whenever we react emotionally to sin, we are full of disgust for what we did. Immediately upon realizing that we let our desires persuade us to commit sins, we are full of shame and remorse. The statement that he will never sin again is not a formal resolution inasmuch as it a natural consequence of a feeling of remorse. God forbid, someone drives without wearing a seatbelt and then gets into a serious accident because he didn’t wear the seatbelt feels stupid and ashamed that he didn’t do something so easy to avoid the serious accident. There is no need for an official resolution that I will never sin again, but it’s obvious based on the emotional feeling of remorse.

However, in chapter two the Rambam describes an intellectual reaction to sin. I don’t feel emotionally disgusted by my sin, but I have a mental awareness of my sin. There is no shame, but intellectually I realize that I made a mistake. What motivates me initially is an intellectual recognition that I did something wrong. Once I have the mental awareness, it’s a battle between the intellect and the emotion, between my intellect and my will to change versus my desire and passion to commit the sin.

When do we emotionally react to sin? Almost immediately when we feel the effects of sin, when we feel disgusted and embarrassed by what we have done. But when do we intellectually react to sin? When do we contemplate our behavior, how we have treated others, how well we have lived up to our commitments to God and to our fellow Jew? This is what Yom Kippur is all about. Yom Kippur is the day designated for the intellectual repentance about which Rav Soloveitchik speaks – the resolve not to sin in the future before the regret.

But Yom Kippur has far greater potential than that. Yom Kippur creates a powerful framework to facilitate an intellectual repentance, but it has a far more ambitious agenda. Let me share the story of Alfred Nobel that I read in “No Regrets.”

“One morning in 1888, Alfred Nobel awoke to a surprise in the morning newspaper. On the pages of the publication, in black and white for all to read, was his obituary. A French journalist had mistaken Alfred’s brother, Ludvig, who had died, for Alfred, who most assuredly had not…

[W]hat really rankled Alfred was how the obituary’s headline encapsulated his life’s work: “Le marchand de la mort est mort” (“The merchant of death is dead”).

Nobel, a Swede who spoke five languages, was an ingenious chemist and an accomplished inventor. And what he invented were things that went boom: detonators, blasting caps, and, most famously, dynamite, which he patented in the 1860s. He built dynamite factories all over the world, which made him a multimillionaire and one of Europe’s most prominent industrialists.

Yet the obit didn’t tell a story of technical genius and entrepreneurial pluck. It described a contaminated soul with a shameful legacy – a greedy and amoral man who became fabulously wealthy by selling people tools for obliterating each other.

Eight years later, when Nobel did die, his will contained a surprise. Instead of leaving his fortune to his family, his estate established a set of prizes for “those who, during the preceding year, shall have conferred the greatest benefit on mankind” – the Nobel Prizes.

The impetus for this gesture, the legend goes, was that premature obituary. Nobel glimpsed a preview of his future and he regretted what he saw. Anticipating this regret, he changed his behavior to avoid it.”

Alfred Nobel’s regret was for something he didn’t do. He sensed from his premature obituary that he was not recognized for doing good in this world.

Yom Kippur is a time when we regret not just mistakes that we made, not just sins that we transgressed, but Yom Kippur is a time when we regret lost opportunities. Rabbi Ari Kahn states (outorah.org/p/23941) that the experience of bringing a korban is intended to lead to a heightened responsibility for our actions. Specifically, the first korban that is recorded in the Torah is the korban olah, which is an expression of regret for the good that was not achieved. The Torah here instructs us that we must constantly ask ourselves not only if we sinned, but if we missed opportunities to do good, because that is what the korban olah is all about. Throughout the year, there is a framework to focus on lost opportunities.

Throughout the year, we have a framework to think about and regret missed opportunities, but on Yom Kippur, this feeling is highlighted throughout the entire day. After all, Yom Kippur is a day when we live an angelic life. The midrash tells us that we are like angels on Yom Kippur. We don’t eat or drink like angels. We stand on our feet like angels. And we are supposed to ask each other for forgiveness and be in a state of peace with all of our fellow Jews, like angels who are at peace with each other. Yom Kippur is a time when we live our idealized self and it’s a time to think about our idealized self and all of the obstacles that stand in our way from achieving our idealized self. In other words, Yom Kippur is a time to dream and then to examine the gap between our reality and our dreams, the missed opportunities that have prevented us from achieving our idealized self.

One of the Roshei Yeshiva of Yeshivat Har Etzion, Rav Yaakov Medan, wrote an article entitled, “Hateshuva mei’cheit ha’shik’chah,” meaning repentance from the sin of forgetfulness. He writes that we need to do teshuva not just from sin, but from a spiritual vacuum, a distance that has been created between us and God. It’s a distance not created from sins; rather, it’s a distance from apathy, a lack of feeling connected to God and that is a real challenge for many in our community. Do we truly feel that connection? Do we constantly look for opportunities to develop our relationship with God through the mitzvah opportunities that He has provided for us? Or do we view mitzvot as a burden and we do what we feel obligated to do, but we lose so many opportunities? That is the teshuva that is so necessary for many of us – the teshuva from the sin of indifference. This is our challenge of regret on Yom Kippur. Not just sins, not just a sinful path, not just sins that require an intellectual teshuva. But on Yom Kippur we need to ask ourselves how many opportunities have we given up to grow as Torah Jews because we were too tired, too busy or maybe too insensitive to utilize these opportunities?

In practice, how do we make regret productive, whether it’s for a sin, a sinful path or a lost opportunity? What does regret combined with resolve for a better future and a plan look like? In his book, “The Power of Regret,” Daniel Pink provides the following strategy: self-disclosure, self-compassion and self-distancing.

First, we need to take the painful step of self-disclosure, of disclosing our regret to ourselves or better yet to a spouse or a good friend. Daniel Pink suggests trying one of the following: write about your regret for fifteen minutes for three consecutive days, talk about your regret into a voice recorder for fifteen minutes for three consecutive days or tell someone else about your regret in person or by phone.

Isn’t self-disclosure what we are doing on Yom Kippur? Isn’t Yom Kippur the day when we announce that we sinned and we say “v’lo shavah lanu” – it was not worth it for us? Isn’t Yom Kippur the day that we need to feel and articulate the damage that our transgressions caused to ourselves and to our souls?

Did you ever think about how you’re feeling when you say the “al cheit’s” on Yom Kippur? Listen, we come to Yom Kippur feeling bad and feeling sinful, but do we truly feel that sinful? Did we really commit all of those sins that we recited in the “al cheit’s?” I know I was bad, but am I really that bad? We try to connect each al cheit to many different types of sins. There are pamphlets that just contain the “viduy,” the confession section of the Yom Kippur davening and in these pamphlets, each “al cheit” represents a whole host of sins of which most of us are guilty. But is that really true? Why should I say “al cheit” for all different types of sins that I may or may not have done and why do I say it again and again and again throughout the day of Yom Kippur? I recite it In the silent shemona esrei, during chazarat hashatz, at maariv, at shacharit, at musaf, at every davening, again and again and again. What is the purpose of all this repetition?

Rabbi Chaim Brovender once explained that we tend to think of ourselves as righteous. We try to protect ourselves and we try to justify any kind of awareness of sin. We have a tendency to mitigate and diminish any wrongdoing that we may have committed. We see ourselves as vindicated because there is a natural resistance to reflecting and judging ourselves. Therefore, there are two aspects to viduy. One aspect of viduy is that I must confess because I sinned, but there is a second aspect of viduy and that is that I confess and I confess and I confess again so that I will repent. It’s not simply the final stage in teshuva. It’s also a first stage in teshuva.

Do you know what this is like? It’s like seeing a therapist. I go to my therapy session and the therapist asks me to talk and he asks me a few questions, but for the most part, I’m just yapping away. I say the same thing again and again and again. While I am yapping away, I am thinking about myself, about who I am and what I can be and the more that I talk and the more that think about myself, I gain greater clarity and at some point, in the fifth session with my therapist, I have an epiphany. I have mental awareness and clarity about what I am doing wrong and what I need to do to change. This is what we are trying to achieve when we recite the al cheit’s. The more that I recite the al cheit’s and the more that I spend that time thinking about my goals and aspirations and how I may have fallen short based on the whole host of sins that the al cheit’s cover, the greater mental awareness and clarity I have about my shortcomings. The al cheit’s of Yom Kippur try to accomplish this first step of self-disclosure.

Next, engage in self-compassion. Daniel Pink writes, “Rather than belittling ourselves during moments of frustration and failure, extend to ourselves the same warmth and understanding we’d offer another person.” Recognize that being imperfect, making mistakes and encountering life difficulties is part of the shared human experience.

God has regret at the end of Parshat Breishit for creating mankind (Breishit 6:6) and it seems very strange for God to have regret. I know that we read in the Torah about a God who speaks and acts, which is a little strange because God is beyond time and beyond space and the only accurate way to describe God is that He is not something we understand. Nevertheless, the Torah sometimes attributes human features to God so that we can relate better to God. But at the end of Parshat Breishit, we read that God has regret, and that is very strange. What does it mean for God to have regret? God is perfect! He doesn’t make mistakes! Why couldn’t the Torah simply have stated that the people were so evil that God decided to destroy the world?

It seems to me that the Torah is trying to tell us that there is something divine about the feeling of regret. We shouldn’t feel bad about having regret. It is part of being human and it is actually somewhat divine, because we grow from regret. We should not ignore these negative emotions, but we should normalize them. What does this look like? Daniel Pink writes, “Well, if a friend or relative came to you with the same regret as yours, would you treat that person with kindness or contempt? If your answer is kindness, use that approach on yourself. If your answer is contempt, try a different answer.” On Yom Kippur, God invites us all to repent and He is kind and merciful to us, so shouldn’t we be just as kind and merciful to ourselves?

Finally, analyze and strategize. The way to do that is through self-distancing. What that means is we zoom out and gaze upon our situation as a detached observer, so we don’t face the negativity on a personal level. Daniel Pink writes, “Imagine your best friend is confronting the same regret that you’re dealing with. What is the lesson that the regret teaches them? What would you tell them to do next? Be as specific as you can. Now follow your own advice… Imagine it is ten years from now and you’re looking back with pride on how you responded to this regret. What did you do?”

Yom Kippur is an opportunity to view ourselves ten years from now, because Yom Kippur is a time when we live out our idealized angelic selves, when we see who we can be and that’s what we must do, analyze and strategize through self-distancing so that we achieve our goals. These are the crucial steps necessary to make regret productive – self-disclosure, self-compassion and self-distancing.

As we approach the end of this teshuva season, I urge you all to seriously consider the power of regret. Regret is only productive if combined with a commitment to future behavior. I hope we all appreciate the opportunity that Yom Kippur provides. Yom Kippur creates a framework for us to extricate ourselves from a sinful path which Rabbenu Yona discussed, Yom Kippur creates a framework for intellectual repentance as Rav Soloveitchik discussed and Yom Kippur creates a framework for the sinfulness of forgetfulness and missed opportunities of spiritual growth which Rav Medan discussed. Yom Kippur also creates a framework for how to regret meaningfully, through self-disclosure, self-compassion and self-distancing.

Wouldn’t it be great if we could list our three biggest regrets from the past year. Three “I wishes.” I wish I lived my own life. I wish I’d spend more time with a certain person. I wish I’d called more. I wish I was less angry. I wish I faced that fear. I wish I wouldn’t have left. I wish I wouldn’t have made it all about me when it was clearly so much bigger than me. I wish I would have joined that shiur, that chesed opportunity. I wish I would have gone to shul more often.

And it’s okay to pray about it and to cry about it. That’s what Yom Kippur is for. And it’s more than okay. It may unlock some hidden strength. Articulate three regrets, but do so with self-compassion, with kindness. If we do this and then plan for the future, then our regret will be reframed as a catalyst for change in the coming months. And then the Biblical word for regret, “nachem,” will be translated into the other meaning of “nachem,” which is comfort. When we regret productively, then our regret can provide us tremendous comfort as it points the way towards a different future, a different ending to our story. My bracha to each and every one of you is that you are successful in tapping into this painful but powerful divine emotion in changing the trajectory of your lives.

Source sheet can be accessed here.