Judaism and No Regrets

“No regrets” is a popular motto, a popular tattoo, and for some, a way of life. Despite its appeal, we are actually 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 God 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.

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. 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 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.” 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 God sitting before these great ledgers and determining where to put our name. However, Rabbi Aryeh Zvi Frimer writes that God 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, attaining a clean slate and start anew.