By: Yael Muskat  | 

Regrets? Bring Them On

This is the season of regrets. In the days surrounding Rosh Hashana, rather than stock up on champagne and confetti, we are asked to regret. This regret allows us to focus on our mistakes, our wrong choices and our shortcomings. Even as I write this, I feel the anxiety, the pit in my stomach. The feelings and thoughts that come with regrets are so painful that the human mind and psyche will try almost anything to avoid them. We will rationalize, distract, blame others or stay in bad situations rather than experience the pain of the realization that “I should not have done that … I wish I did that ... I made a bad choice … If only I would have…” 

We have to feel the pain. We can run but we can’t hide, and by the time Yom Kippur comes, we are faced with an analysis of our deeds and the regrets about what was done wrong or what was left undone. Is this intended to make us suffer? Do we have to just get through it, or can we actually find a way to suffer a little less or to even look forward to it? 

The truth is, that despite all of our efforts to avoid regrets, regrets take up a large part of our emotional life. A study1 of over 17,000 people showed that over 80% of them have had regrets throughout their life, and over 45% have them often. Another study2 showed that of all difficult emotions, such as anger, sadness, boredom and fear, regret was the one they experienced the most. At the same time, despite the difficulty of it, if done right — and that’s a big if — regret is also the feeling that people said they valued the most. Study after study shows that examining the past leads to a better future3.

Judaic tradition agrees. This season is not only the season of regrets; it is the season designated for teshuva, and regret is at the heart of the teshuva process. Teshuva, which literally means “return,” is defined as the process of repentance. Rabbi Jonathan Sacks described it beautifully, saying teshuva is much more than repenting for a laundry list of sins to avoid punishment; rather, it is a time of “profound liberation.” 

If regret is supposed to enable us to achieve true personal liberation, how do we do regret “correctly”? As a psychologist, I’m always on the lookout for “hacks,” or tools for my proverbial “toolbox” to help me crack the stubborn negative feelings and thoughts that “stick,” and regret is on top of the list. So, when I recently stumbled across a book on this topic, I was hopeful that it would lend me that much-needed perspective. And it didn’t disappoint. Daniel Pink’s “The Power of Regret: How Looking Backward Moves Us Forward” intrigued me immediately, simply based on its title. In the book, Pink shares fascinating insights on why we regret and what regret has to offer based on years of research. The book particularly touched me because of how deeply and beautifully it dovetailed with what Torah sources and Jewish tradition teach about teshuva and regret. 

The book is full of fascinating insights, but I will focus on the ways in which Pink’s description of “good regret” connects directly with the steps of teshuva in our tradition and as described by the Rambam in Hilchos Teshuva, Chapter 1. Separating from the sin indicates that the person is not currently engaging in the behavior, and is a basic foundation for teshuva. There are three other elements that are more psychological: confession, regret and resolve not to sin again. Pink’s expansive definition and prescription for how to regret touches on all three of these psychological components. 

  1. Confession: A surprising parallel between the psychology of regret and the experience of teshuva is that of confession, or vidui. Pink asserts that “the first step in reckoning with all regrets, whether regrets of inaction or action, is self-disclosure.” He explains that we may avoid telling others or speaking about behaviors or decisions that we regret, but that there is “an enormous body of literature that makes it clear that disclosing our thoughts, feelings and actions, by telling others or simply by writing about them, brings an array of physical, mental and professional benefit.” He recommends habits such as having a regret circle, a gathering with close friends to discuss mutual regrets, or having a “regret resume” with a list of things we regret, because the very act of this disclosure without judgment will propel you to future action and growth (Pink, pg 183).

Just as Pink recommends verbalizing our sins even to ourselves, the Rambam enumerates confession as a key component to teshuva. We are required to verbally state the sins that we have committed. When we do this, we take the first step to action. We take responsibility, but we also name the problem and by doing so we put a limiting factor on it. Rav Soloveitchik called the vidui, the confession, the first act of teshuva in that it is a cry to God. The act of confessing is a call for help and it reflects a desire to change. In his essay, “On Repentance,” Rav Soloveitchik writes, “The Vidduy is the call, the request to come back and stand in front of God’s countenance, His face, look at Him and summon the courage to confess.” 

  1. Regret: Regrets are made up of feelings and thoughts. The feelings associated with regret are the pit in the stomach, the feeling of panic, or the sinking heart. One way to look at it is that the feeling of regret is actually the pain of loss, loss of what could have been, or loss of an opportunity. Science shows that our minds are wired to look at past events and have regrets that are painful. But, Pink warns, “Don’t push away the feeling: Welcome the feeling of regret; it can propel us forward and improve our lives.” He explains that one must feel regret to grow from it and to change. As an example, CEOs who were asked to confront their regrets about a negotiation ultimately improved their “decision making hygiene” and made more informed, thoughtful decisions going forward (Pink, pg. 43). If we simply push away the feeling of regret, then we don’t give ourselves the opportunity to know what we want or need to change. 

Similarly, the Rambam states that a crucial step for teshuva is to feel regret, or to experience charata. When it comes to teshuva, Rav Soloveitchik explains that sin separates us from G-d, and the pain associated with teshuva is that loss of closeness and connection with God4. Rabbi Sacks5 reiterates this point, stating that “sin alienates, it distances us from G-d, and the result is that we are distanced from where we ought to be, where we belong. We become aliens, strangers.” Teshuva is a process of “restoring our relationship with God.”

  1. Resolve not to sin again: There is a danger in regretting too much. Rumination, or overthinking about past mistakes, can lead to severe negative psychological consequences. Pink warns, “don’t dodge the emotions, but don’t wallow in them either. Confront them; use them as a catalyst for future behaviors”6. One key component to preventing rumination is managing the thoughts underneath the emotions. It is crucial to view the mistake not as “who we are” but as a “specific mistake in a specific situation.” For example, if you were late for prayer services and you were upset about it, you could think, “I’m always late… I am not a good person… I am not worthy of praying...” or you can say, “I was late this morning… I don’t have a good system for waking up in the morning… Let me examine what is causing this and how I can fix it.”

To fight rumination, in addition to reframing the thought, the key to successful regret and teshuva is to transform the feelings and thoughts into action. The secret is that after we feel the feelings, and have the right thoughts, regret is only useful if it is connected to an action plan. If possible, Pink recommends making amends, fixing the problem, reaching out to the person you lost touch with and creating better systems to do better. At times, it isn’t possible to make amends or to fix something in the past, but it is just as powerful to use the past to make a plan to change, to do better in the future, by creating concrete steps to do things differently. This idea dovetails beautifully with the teshuva component of resolving to do better in the future, which can only be done with an action plan.

It is gratifying that psychological findings support our long held traditional beliefs about the benefits of teshvua, with regard to confession, regret and resolving not to sin again. However, to me, the most stunning revelation of the book was the way in which Pink elevated regret to being more than healthy, but actually redemptive. 

This approach to teshuva and the opportunity of regret brings to mind for me the famous description of Elul being a time of “ani ledodi vedodi li,” a time for closeness and love between man and God. God, as it were, is holding our hand while we go through this difficult but ultimately redemptive process. The prescription for regret isn’t easy. It isn’t supposed to be. But it’s the key to building a better tomorrow and restoring ourselves to the people we can truly be. The pain we feel is actually a gift. It’s the nudge to push us to improve. Let us find the strength not to ignore it, and also not to buckle under it, but rather to grow and redeem ourselves through it. 

Yael Muskat, PsyD is Dean of Mental Health and Wellness and Director of the Yeshiva University Counseling Center.

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  1.  Pink, Daniel, et al. American Regret Project (2021)
  2.  Saffery, Colleen, Amy Summerville, and Neal J. Roese. “Praise for regret: People value regret above other negative emotions." Motivation and Emotion 32, no.1 (2008): 46-54
  3.  Pink, D.H. (2022) The Power of Regret: How Looking Backward Moves Us Forward. New York: Riverhead Books
  4.  Peli, P.H. (2000) On Repentance: The Thought and Oral Discourses of Rabbi Joseph Dov Soloveitchik. Reprint, Maryland: Jason Aronson Publishers
  5.  Saks, J. (2017) Ceremony and Celebration: Introduction to the Holidays. Jerusalem, Maggid Books.
  6.  Kray, Laura J., Adam D. Galinsky, and Keith D. Markman. “Counterfactual structure and learning from experience in negotiations.” Journal of Experimental Social Psychology 45, no.4 (2009) 979-82


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