A Coach Approach to Teshuva

A story is told (“Touched by a Story” by Rabbi Yechiel Spiro, pp. 81-83, Artscroll Mesorah) about a young man who was studying in Rabbi Shimshon Pincus’, zt”l, yeshiva in Ofakim, Israel. The boy, a 17 year old named Meir, was disappointed with his spiritual preparation for the High Holidays. On the morning of Rosh Hashana, the rosh yeshiva found Meir sitting despondently in the hallway. After inquiring about the reason for the boy’s sadness, Meir told Rav Pincus about his struggles to improve and his continued failures in this regard.

Rav Pincus listened sympathetically. He then related the following powerful incident. During the Yom Kippur War he had brought his daughter to Shaarei Tzedek Hospital in Jerusalem to have a deep cut treated. While they were there, they heard a tumult in front of the emergency room. Upon inquiring, Rav Pincus was told that a soldier had been brought in with a gunshot wound in his leg. After completing surgery to remove the lodged bullet, the operating doctor informed the soldier that he was free to return home to recuperate.

The solider grimaced as he slid off of the operating table. He then looked at the doctor and asked incredulously, “Home? You think that I am going home? True I was shot and lost this battle. But there’s a war raging out there and my fellow soldiers need me back on the battlefield.” With that, he made his way back to the front lines.

Rav Pincus turned to Meir and said that while he may have stumbled and even lost a few battles along the way, the war against the yetzer hara (evil inclination) rages on, both individually and collectively. “We’re fighting a war in (the bais midrash) and I don’t want to head back in there without you. We need you to fight alongside the rest of us.” And with that, Meir walked with his rebbi to continue their prayers.


Teshuva is on the forefront of our collective minds as we near Yom Kippur, the holiest day of the Jewish year. Our sages tell us that those who seek to engage in teshuva are actively assisted from above. (Shabbos 104a; Yoma 38b) Nothing can stand in the way of the remorseful soul that seeks to return, particularly on Yom Kippur, which offers a unique opportunity to break through our spiritual barriers and come clean.  

For many of us, the weeks spent reciting selichos and engaged in introspection helped us approach this sacred Day of Atonement with a renewed sense of purpose and appetite for change. Such individuals are ready to seize the moment and use the incredible gift of Yom Kippur to the fullest degree possible. But many others do not feel quite ready and struggle with the fact that they have lost many “battles” along the way. What can we do to ensure that this year’s teshuva process will help us win the war by inspiring change that doesn’t fall flat and instead impacts our behavior for the long haul?

As an executive coach, I would like to respond to this question by using what is often referred to as a “coach approach”. Coaches promote change by helping clients expand their awareness and develop their own approach to solving a problem. They believe that the answers to the most difficult questions lie within us and that we can identify solutions with proper guidance and support. In the paragraphs that follow I will share some coaching techniques that may help all of us make the most out of Yom Kippur.  

There are five basic elements of teshuva: hakaras hachet (recognition of one’s sins as sins), charata (remorse), azivas hachet (“abandoning” or desisting from sin), pei’raon (restitution, where possible), vidui (confession). One final step to ensuring a positive, sustained outcome is to make a kabbalah al he’asid (commitment to not repeat sinful conduct).

Let’s begin with the first element: hakaras hachet. In order to engage in repentance we have to acknowledge the folly of our ways. This is not as simple as it may seem. First of all, we do not always recognize the sinful nature of our actions, such as when we speak lashon hara thinking that our words are permitted or hurt someone’s feelings unwittingly. In addition, our sages tell us that, “ovar v’shana naaseh lo k’heter” (if we sin repeatedly the actions become viewed in our minds as permitted). We often find ourselves slipping into a routine that we eventually come to justify. In such situations it can be easy for our yetzer hara to get a hold of us and say that we have no hope. We are too far along, he’ll argue, on our deviant pathway to ever turn things around.

In order to overcome such thinking we need to realize that error and sin are as central to the human condition as any other quality. We all make mistakes and will do so every day of our lives. We must be willing to accept them and have the self-confidence and integrity to admit it when we do. Our ability and willingness to do this, perhaps more than anything else, will allow us to take control of our teshuva process and our lives in general.

Once we have come to terms with our sinful conduct, we typically begin to feel charata (regret). Whether the victim of our deeds is another person or Hashem (or both), we need to be able to express our regret clearly and without condition. To do that, consider following these steps:

  • Apologize sincerely – Saying “I am sorry” must communicate genuine regret for your behavior and a wish that you had acted differently.
  • Take complete ownership – Avoid shifting the blame (“I apologize that you misunderstood me,” “I am sorry that you felt that way,” etc.). Doing so greatly diminishes the apologizer’s effectiveness. Stating that the other person was partly responsible for what occurred or for his hurt feelings places the listener on the defensive, and causes them to consider you to be disingenuous and perhaps even accusatory. And that is no way to apologize.
  • Avoid excuses – State your error directly, without justification. To the listener’s ear, excuses not only feel like an attempt to validate the wrongdoing, they may even sound like an attack, as if the plaintiff was inconsiderate to hold him accountable in the first place.
  • State how you intend to fix things – Articulating your intent to correct matters, including restitution (pei’raon) where needed, will do wonders to convince the listener of your sincerity. It should be simple, realistic and detailed.
  • Follow through – Few things damage a relationship more than when a person sets expectations for change and then does not follow through. In many ways, it is worse than not having apologized in the first place. When we do not act as promised, others question our will and our trustworthiness.

The step following regret and apology – known as azivas hachet (“abandoning” or desisting from sin) – may be the hardest one of all. As we noted above, once we start along a path of poor behavior we can find it hard to get unstuck.

Rabbi Paysach Krohn (“Reflection of the Maggid”, pp.262-263, Artscroll Mesorah) relayed a thought from Rabbi Shlomo Teitlebaum of Kew Gardens, New York. Rabbi Teitlebaum was once in the Bronx Zoo when he heard a ferocious roar. He recognized it as being a lion’s, but felt no fear. He knew that the lion was held in a cage and posed no threat to him or others.

Rabbi Teitlebaum then considered our response to the days of “Aryeh” (a lion, also an acronym for Elul, Rosh Hashana, Yom Kippur, and Hoshana Rabbah). When we fail to hear the “roar” of these auspicious days, it may be because we have erected a sizable barrier between us and our Maker, making it difficult to feel inspired to change our ways.

How can we be sure to knock down those barriers and get over the spiritual hump? You may want to consider using powerful, vivid imagery, just as Hashem did when He first introduced the avodah of Yom Kippur.

The beginning of parshas Acharei Mos details the avodah of Yom Kippur. However, it frames the directive of Hashem to Moshe as having occurred in the direct aftermath of the deaths of Aharon’s two sons, Nadav and Avihu. “And the Lord spoke to Moshe after the death of Aharon's two sons, when they drew near before the Lord, and they died. And the Lord said to Moses: Speak to your brother Aharon, that he should not come at all times into the Holy within the dividing curtain, in front of the cover that is upon the ark, so that he should not die, for I appear over the ark cover in a cloud.” (Vayikra 16:1-2)

We know that the Torah does not always present information sequentially (ain mukdam u’meuchar baTorah). The fact that it chose to record these two concepts in sequential fashion indicates that a particular relationship exists between the two. What was that connection?

To answer this question, Rashi shares a famous parable that underscores the power of using real-life examples to drive behavioral change.  

And the Lord spoke to Moshe after the death of Aharon's two sons, when they drew near before the Lord, and they died. (Vayikra 16:1) What does this teach us [when it specifies “after the death of Aaron’s two sons”]? Rabbi Elazar ben Azariah illustrated [the answer] with a parable of a patient, whom a physician came to visit. [The physician] said to him, “Do not eat cold foods, and do not lie down in a cold, damp place.” Then, another [physician] visited him, and advised him, “Do not eat cold foods or lie down in a cold, damp place, so that you will not die the way so-and-so died.” This one warned that patient more effectively than the former. Therefore, Scripture says, “after the death of Aharon’s two sons.” [Rashi, ibid, quoting Toras Kohanim 16:3]

Nadav and Avhiu died because of a flaw associated with their attitude and / or conduct when they entered the mishkan. The Torah chose this opportunity to reinforce that the mishkan was not meant to be entered by any person at any time, but only by the right person at the right time. Any misstep in this regard could be fatal.

Still, we need to understand why Hashem chose to introduce the topic of Yom Kippur in such negative fashion. Even if it was necessary to deliver such an admonition, couldn’t it have waited until a later part of the discussion, after we better understood and appreciated the actual avodah? Why not first emphasize the positives, such as atonement and purity, and then cycle back to any related warnings?

The Torah is teaching us a lesson in the importance of using imagery to influence personal change. In order to properly approach the singular day of Yom Kippur and its tremendous power, it was important to first emphasize its unique holiness. This holiness could best be comprehended by envisioning the consequence of its violation, as evidenced by the deaths of Aharon’s two great sons. With that framework in place, everything that would follow would take on a new dimension of seriousness and sanctity.

This leads us to the final piece, kabbalah al he’asid (commitment to not repeat sinful conduct). Our “New Year’s Resolutions” need to be a serious undertaking, with a real commitment for change. One strategy that I use often with clients who seek to make change in their lives is to have them set S.M.A.R.T. goals. “S.M.A.R.T.” stands for specific, measurable, attainable / realistic and time-related.

  • Specific – well defined, you know exactly what you seek to achieve;
  • Measureable – quantifiable in a way that helps determine whether the goal has been achieved;
  • Attainable / Realistic – a goal that is within reach, largely because of your deep desire to attain it;
  • Time-related – set to a timeframe to ensure continued, focused efforts towards attainment.

A person, for example, who seeks to daven with greater concentration, fervor and awareness, would be wise to apply this formula. Set specific goals of what you would like to work on that allow you to focus your energies. Determine how you will measure success, in terms of ability to translate more words, sustain concentration for extended periods, etc. Make sure that the goals that you set are attainable and not beyond the pale of what is presently realistic (this, of course, can and should change as you grow in this area). Then set a timeframe for your goal to keep you on task and moving in the right direction.


In conclusion, I leave you with the thoughts of Rav Eliyahu Dessler. Rav Dessler (Michtav M’Eliyahu, Vol II, pp. 96-97) writes that our judgment ultimately rides on the inner desires and motivators that exist within our hearts. He supports his argument by citing Ramban in Parashas Emor, who writes that Rosh Hashana is a “yom hadin b’rachamim” and Yom Kippur a “yom harachamim b’din.”

The explanation to Ramban’s words, says Rav Dessler, is as follows. Despite the seriousness of Rosh Hashana, we have the capacity to stir divine mercy on that holy day by demonstrating such qualities of giving and compassion towards others. Conversely, we have the ability to transform the compassionate day of Yom Kippur into one of strict judgment if we are unable to engage in meaningful change.

As we approach Hashem on Yom Kippur, we should aspire to give Him every opportunity to view us as individuals who are on an upwards trajectory, deserving of inscription and sealing in the Book of Life. I wish us all a k’siva v’chasima tova.

Naphtali HoffComment