Mazeltov to Andrew and Lee King on Daniel and Joshuas Barmitzvah and mazeltov to grandmother, Roslyn Kramer.
Why regret is an essential element to real change: by Rabbi Efrem Goldberg

Why regret is an essential element to real change: by Rabbi Efrem Goldberg


“No regrets” is a popular motto, a popular tattoo, and for some, a way of life. Despite its appeal, we are hard-wired to experience regret – and that is a good thing. 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 respondents 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.

Regret is the first primary component of the repentance process performed on Yom Kippur. Does that mean we’re supposed to beat ourselves up be racked with shame and guilt? Or does regret serve a different purpose?

No regrets doesn’t mean living with courage, it means living without reflection.

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 Judaism 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 G-d to eliminate mistakes, not to wipe out 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.


  1. 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 analyse them, limit them, learn and ultimately grow from them. Vidui, the verbal confession that is recited numerous times during Yom Kippur, acknowledges mistakes and shortcomings, and is an indispensable, perhaps the most critical, element of teshuva, repentance.

We cannot correct and repair ourselves without articulating our regrets. Only when we disclose it, confront it, and analyse it can we learn from it and move on from it.

  1. 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.” After regret, the next step in repentance is called in Hebrew kabbalah al ha’atid, extracting a lesson for the future, giving the regret meaning by turning it into positive action. We pivot from those wrong decisions, actions, or feelings and redirect our priorities, focus, and choices.

Three Months to Live

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!”

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 repentance.”

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.

Editing Your Book of Life and Death

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.

On Yom Kippur, the Book of Life and the Book of Death are open. We typically think of G-d sitting before these great ledgers and determining where to put our name. However, Rabbi Aryeh Zvi Frimer writes that G-d 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 Book of Life, 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 experiment in Manhattan, the researchers wiped the chalkboard clean and wrote “Clean slate” across it. On Yom Kippur, as we feel regret, we can edit our Books of Death and Life and pivot, accordingly, Ha’azinu 5781: Atonement = To Be One With


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Three Steps to Finding Forgiveness

As mentioned last week, Rosh Hashanah begins the Aseres Yemei Teshuvah – commonly translated as the Ten Day of Repentance. In actuality, the word teshuvah means “return,” but it is often mistranslated as “repentance.” These Ten Days of Returning begin with Rosh Hashanah and end with Yom Kippur – the Day of Atonement, often referred to as the holiest day of the year.

This is a very unique concept and an absolute kindness and gift from the Almighty. Teshuvah actually offers mankind the one thing no one really believes is possible to achieve: The ability to change the past.

Maimonides, the great medieval philosopher and codifier of Jewish law, rules that it is a mitzvah – a positive commandment – to repent. In other words, the Almighty Himself is asking us to return to Him. As we shall soon see, there is a very powerful message here, one that we must try to internalize. Indeed, the very success of accomplishing the essence of Yom Kippur can only be achieved by understanding this concept.

“This shall be an eternal decree: …on the tenth of the month you shall afflict yourselves and all manner of work you shall not do, neither the native born nor the convert amongst you. For this day, he [the Kohen Gadol, the High Priest] shall atone for you to purify you from all of your transgressions – before the Almighty you shall be purified” (Leviticus 16:29-30).

As mentioned above, the Torah states that we shall “afflict ourselves” on Yom Kippur – the Day of Atonement. According to Jewish law there are five “afflictions” that we must observe on Yom Kippur. We are prohibited from 1) eating and drinking 2) wearing leather shoes 3) marital relations 4) anointing the skin with salves and oils, and 5) washing for pleasure.

Yom Kippur is the anniversary of the day Moshe brought the second set of Ten Commandments down from Mount Sinai. This signified that the Almighty forgave the Jewish people for the transgression of the Golden Calf. This day was thus decreed to be a day of forgiveness for our mistakes.

However, this refers to transgressions against the Almighty. Transgressions against our fellow man require us to correct our mistakes and seek forgiveness. If one took from another person, it is not enough to experience regret and ask the Almighty for forgiveness; first, one must return what was taken and ask for forgiveness from the person and then ask for forgiveness from the Almighty. G-d does not forgive a person for sins committed against another person unless the injured party offers forgiveness first.

The actual process of teshuvah is made up of four parts. 1) Regret: We must recognize what we have done wrong and regret it. 2) Cessation: We must stop doing the transgression. 3) Confession and Restitution: We must verbally confess and ask the Almighty to forgive us. We must correct whatever damage that we can, including asking forgiveness from those whom we have hurt – and making restitution, if due. 4) Resolution: We must accept upon ourselves not to do it again in the future.

A key component of the liturgy of The Ten Days of Repentance (Returning) and Yom Kippur is known as the 13 Divine Attributes of Mercy. The ancient source of this prayer is rather astonishing: The Almighty Himself taught it to Moses for him to teach it to the Jewish people as a way to seek forgiveness.

​And the Lord passed by before him, and proclaimed, “Hashem, Hashem, omnipotent, merciful and gracious, slow to anger, and abundant in kindness and truth, keeping mercy for thousands, forgiving iniquity and transgression and sin…” (Exodus 34:6-8).

The Talmud (Rosh Hashanah 17b) states, “There is a covenant (between G-d and His creations) that a prayer that contains the Thirteen Attributes of Mercy will never go completely unanswered.”

Even more remarkably, the very same passage in the Talmud describes the scene that unfolded between G-d and Moses; “Rabbi Yochanan said ‘had it not been an explicit verse in the Torah it would be impossible to even utter’ – the verse is coming to teach us that the Almighty wrapped Himself in a tallit (prayer shawl) like a shliach tzibbur (a cantor who leads the congregation in prayer) and demonstrated to Moses the order of the prayer. Hashem then told Moses; ‘Any time that the Jewish people sin they should recite this prayer and I will forgive them.’”

Obviously the Talmud is telling us that it is very difficult to conceive of the Almighty dressing up and giving a demonstration of how to seek forgiveness from Him. Yet that is exactly what happened. So we are left wondering what exactly was the point of G-d dressing up and acting it out for Moses? Why would Moses be in need of a visual demonstration? What message was G-d conveying to Moses?

Generally, asking forgiveness from someone is very difficult. It requires an admission of wrongdoing or, at the very least, communicating that the intention wasn’t to harm. But the most daunting part, and usually the reason that people procrastinate asking for forgiveness, is because of the uncertainty of how the injured party is going to react.

Will that injured person yell and scream at me? Or worse, will they try to use my admission of guilt as a way to take advantage of me in some way? The anxiety of these potential consequences usually prevent one from making the effort to mend fences.

Now consider a different scenario: How would you feel if someone would come to you and let you know that the person you injured feels badly because this incident has created a rift in the relationship and that this person really just wants to talk and make up with you? Suddenly it becomes a lot easier to make that phone call.

It is for this very reason that the Almighty took the extraordinary steps in demonstrating the path to forgiveness. The purpose of the “show and tell” demonstration was so that Moses would understand and convey to the Jewish people, that Hashem Himself is leading the path to His forgiveness. In other words, Hashem – who is the injured party – is willing to lead the congregation in prayer because more than anything He wants His children, the Jewish people, to return to Him.

Hashem is communicating to Moshe that there should be no barriers to asking for forgiveness because Hashem Himself wants to fix the relationship. It is for this reason that a proper prayer of forgiveness will always be answered. G-d is, in essence, telling us that He is always waiting for us to come home to Him and asking us to return.

On Yom Kippur afternoon we read the Book of Jonah (i.e. “Jonah and the Whale” – though it was some sort of a fish and not a whale). The essence of the story is the same theme that we saw above. G-d was concerned that the ancient city of Nineveh was steeped in sin and deserved annihilation. G-d therefore asked Jonah to go inform the city that they must immediately repent or face the consequences. (Interestingly enough, Jonah initially refused the mission on the grounds that if the inhabitants of the city of Nineveh, who weren’t Jewish, would readily repent, then this would reflect badly on the Jewish people in Israel who were also steeped in sin and hadn’t repented.)

As a final point on the subject of Yom Kippur, after making a tremendous effort to seek forgiveness from those who we have injured, make restitution, and seek forgiveness from G-d, we must then ask ourselves the following question:

“What can I do in the future to improve my relationship with the Almighty and my observance of His commandments? What affirmative steps can I take to build a better connection with the Almighty? How can I become a better person, spouse, parent, or child? What can I do to help my community and mankind?”

Obviously, the answers to these questions are always going to be a work in progress. But that is the true beauty of our lives; the ability to become more and strive for ever greater heights. Wishing my readers all over the world a most meaningful fast and Yom Kippur experience, and a G’mar Chatima Tova, attaining a clean slate and start anew.

2020 Sandton Shul Batmitzvah Ceremony