Regrets or No Regrets?

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“No regrets” is a popular motto, a badge of honor, and for some, a way of life.  It is even a popular tattoo, a slogan people literally engrave on their skin.  Despite its appeal, it turns out living the “no regrets” life isn’t really possible; we are actually hard-wired to experience regrets and that is a good thing.  You see, regret doesn’t just make us human, it can also make us better.  Brene Brown, the popular professor and author, puts it well: “No regrets’ doesn’t mean living with courage, it means living without reflection.”


A few years ago, a group of researchers put up a chalkboard on a New York City street and asked random passersby to write down their biggest regrets. The respondants were from different walks of life, but their regrets all had one alarming thing in common: the word “Not.”  They were primarily about chances not taken, about words not spoken, about dreams never pursued.  By the end of the day the chalkboard was completely filled with tales of regret.


We aren’t in New York City and there is no chalkboard here, but make no mistake, we are here today on Yom Kippur to express our regret, what we wish we could have done differently, mistakes we made, things we want to retract. 


Rabbeinu Yonah writes in Shaarei Teshuva:

עיקרי התשובה: העיקר הראשון – החרטה. יבין לבבו כי רע ומר עזבו את ה'

The first primary component of the repentence process is regret. One must recognize in his heart the sinfulness and bitterness of departing from Hashem.


What is charata and what role does it have in teshuva? Are we meant to beat ourselves up, knock ourselves down, be racked and riddled with shame and guilt, or does charata serve a different purpose?


Last year, Daniel Pink published a book called “The Power of Regret” in which he writes: “The conclusion from both the science and the survey is clear: Regret is not dangerous or abnormal. It is healthy and universal, an integral part of being human. Equally important, regret is valuable. It clarifies. It instructs. Done right, it needn’t drag us down; it can lift us up.” 


Pink found that to make our regrets work for us, we must respond systematically by neither avoiding them nor perseverating over them. He says there are three critical steps that corelate with what the Torah has already taught:


1. Reframe your regret.  Does what you regret deserve kindness or contempt? Does the regret represent a moment in your life, or does it define your life?  We ask Hashem yitamu chataim, eliminate mistakes, but not chotim, those who make them.  Even as we spend today confronting what we have done wrong, it is critical that we recognize they need not define us.


2. Disclose your experience and regret -  Pink argues that using language, whether written or spoken, forces us to organize and integrate our thoughts. Instead of those unpleasant emotions fluttering around uncontrollably, language helps us analyze them, limit them, learn and ultimately grow from them.  The Rambam sees vidui, verbal confession, acknowledging mistakes and shortcomings, as an indispensable, perhaps the most critical, element of teshuva. 


The Alter Rebbe connects the word charatah with charitah, engraving.  We have to admit what we regret so that we can engrave what we learned and ensure we don’t repeat it.  We cannot correct and repair ourselves without articulating our regrets.  Only when we disclose it, confront it, and analyze it can we learn from it and move on from it.  


3. Extract a lesson. – Lastly, Pink says don’t marinate, perseverate or get stuck.  The subtitle of the book is, “How looking backward moves us forward.” The Rambam says the step in teshuva after charata is kabbalah al ha’asid, extracting a lesson for the future, giving the regret meaning by turning it into positive action. Like the Alter Rebbe, the Alexander Rebbe links charata, regret, to charita, engraving, as in the pasuk in Yeshaya (8:1) b’cheret enosh, man engraved. Charata is an invasive process where we scrape away our most detestable and despicable traits until they are gone.


For the Alexander Rebbe, charata, regret, is not about the past, it is about knowing what to purge and cleanse and repair in the present. We can’t undo what we regret but we can learn and grow from it by changing our behavior now.  


In his formula for return and repair, the Rambam delineates the importance of regret, only he uses a different term. 

וּמַה הִיא הַתְּשׁוּבָה. הוּא שֶׁיַּעֲזֹב הַחוֹטֵא חֶטְאוֹ וִיסִירוֹ מִמַּחֲשַׁבְתּוֹ וְיִגְמֹר בְּלִבּוֹ שֶׁלֹּא יַעֲשֵׂהוּ עוֹד …וְכֵן יִתְנַחֵם עַל שֶׁעָבַר …וְיָעִיד עָלָיו יוֹדֵעַ תַּעֲלוּמוֹת שֶׁלֹּא יָשׁוּב לְזֶה הַחֵטְא לְעוֹלָם …וְצָרִיךְ לְהִתְוַדּוֹת בִּשְׂפָתָיו וְלוֹמַר עִנְיָנוֹת אֵלּוּ שֶׁגָּמַר בְּלִבּוֹ:

The word “ִתְנַחֵם” is often translated as “regret”, but it shares the same shoresh as the word for “console”.  When Hashem is saddened by the behavior of humanity after creating the world the Torah says וַיִּנָּחֶם ה' כִּי עָשָׂה אֶת הָאָדָם בָּאָרֶץ. When Hashem is worried we will regret leaving Egypt, he took us a circuoutous route, כִּ֣י ׀ אָמַ֣ר אֱלֹהִ֗ים פֶּֽן־יִנָּחֵ֥ם הָעָ֛ם בִּרְאֹתָ֥ם מִלְחָמָ֖ה וְשָׁ֥בוּ מִצְרָֽיְמָה׃


Hashem is perfect, infinite, and omnipresent. How is it possible for Him to have “regret?”  It must be נָחָם doesn’t mean regret in the way we clasically think of it, but it means to pivot, to redirect. When performing nichum aveilim we aren’t assisting the mourners in regret, we are encouraging them to pivot and redirect their lives, now without their loved one.  In the context of Teshuva, מִתְנַחֵם  isn’t merely recalling the past and feeling bad and sad about it, but rather it is a process wherby we pivot from those decisions, actions, or feelings and redirect our priorities, focus, and choices.


In the process of teshuva, regret isn’t merely an emotion, it is a dynamic process whereby we replace the remorse-worthy act with an active commitment to “remove the mark” of that mistake currently embedded within us.


It was 2005. At 53-years of age, Eugene O’Kelly was full of life. As the chairman and CEO of KPMG, one of the largest U.S. accounting firms, O’Kelly was the consummate global jet-setter. His successful career brought him into the presence of Warren Buffet and other business giants. Gene spent days, nights, and weekends planning the firm’s continued success. He described himself as feeling, “vigorous, indefatigable, and ... near immortal.”


In the spring of 2005, Eugene’s wife, Corinne, noticed that the right side of her husband's face was sagging. He went to see a neurologist and within a week, Gene was diagnosed with inoperable, late-stage brain cancer. He was given three months to live. With this sudden and shocking diagnosis, Gene had to quickly determine how he would spend his remaining 100 days on earth. He made an immediate decision to make every minute of his life count. 


Gene wrote that he wanted “every calculated step to be filled with truth of purpose.” Gene struggled to live in the moment as he began a process he called “unwinding.” Bidding farewell to friends and loved ones not only spurred Gene to recall happy memories but kept his “focus on life, not death.” They guaranteed that he was “almost always thinking about what mattered.”


For those considering taking the time someday to plan their final weeks and months, Gene had three words of advice: "Move it up!" 


The gemara in Shabbos (153a) says:

  רַבִּי אֱלִיעֶזֶר אוֹמֵר: שׁוּב יוֹם אֶחָד לִפְנֵי מִיתָתֶךָ. שָׁאֲלוּ תַּלְמִידָיו אֶת רַבִּי אֱלִיעֶזֶר: וְכִי אָדָם יוֹדֵעַ אֵיזֶהוּ יוֹם יָמוּת? אָמַר לָהֶן: וְכׇל שֶׁכֵּן, יָשׁוּב הַיּוֹם, שֶׁמָּא יָמוּת לְמָחָר, וְנִמְצָא כׇּל יָמָיו בִּתְשׁוּבָה

Rebbe Eliezer says “Repent one day before you die.” His students asked him: “But does a person know which day he will die?” He responded: “Therefore he must certainly repent today, for maybe he will die tomorrow – in this manner all his days are spent in repentence.”


Don’t wait to unwind your life – move it up! Tell friends who have enriched your life, thank you. Ask those whom you have hurt or disappointed for forgiveness.  Identify your regret, reframe it, extract a lesson, and make a correction by redirecting yourself. 


Gene did one more thing in those last three months — he wrote a book called “Chasing Daylight.” It’s a moving and humbling narrative describing Gene’s search for a better way to die. He opens the book by saying, “I was blessed. I was told I had three months to live.” He writes that he worked hard so he could spend retirement with his wife — a goal that suddenly vanished with his diagnosis.


Chazal tell us that on this sacred day, Sifrei Chaim and Sifrei Meisim, the book of life and the book of death, are open.  We typically think of Hashem sitting before these great ledgers and determining where to put our name.  However, the Koshoglover, Rav Aryeh Zvi Frimer, writes in his Eretz Tzvi that Hashem isn’t the only author in these books.  On this special day, we decide what we want to write into the book of death, things that we want to let go of, destroy, put behind us. And we decide what to write in the sefer ha’chaim, what we want to give life to, learn from, grow from and build a future from.  


Regrets guide us in this editorial process as we choose the relationships, habits, and experiences that need unwinding and those that we need to lean into in order to lead a meaningful life.  Regret is not a time machine, we can’t undo the person, parent or spouse we were, but we can still determine the person we will have yet to be.


Gene spent many precious hours writing his book fully cognizant of his fundamental limitation — he would be unable to write the final chapter. In finishing the book that her husband began, Gene’s wife, Corrine, reflected on how Gene was so concerned about how to say goodbye to their teenage daughter: “He worked so hard to find the perfect trip or gesture or gift for her to have the rest of her life… but how is that ever possible? How do you unwind a relationship with your child who is only 14?”


In his final days, Gene had one profound regret:  “Had I known then what I knew now, almost certainly I would have been more creative in figuring out a way to live a more balanced life, to spend more time with my family.”


At the end of the experiement in Manhattan, the researchers wiped the chalkboard clean and wrote “Clean slate” across it. Today, we aren’t writing regrets on a chalkboard but as we feel charata, we can practice charita - engraving our regrets on our hearts as we klop al cheit shechatanu lefanecha. If we properly edit our books of death and of life and pivot accordingly, at the end of today, we, too, get a clean slate, a fresh start, as Hashem promises us: Salachti Kidvorecho.