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. 

Finally, there is kabbalah al he’asid, a firm commitment not to repeat sinful conduct. Our “New Year’s Resolutions” need to be a serious undertaking, with a real commitment to 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.


Rabbi Naphtali Hoff is an executive coach and president of Impactful Coaching and Consulting (ImpactfulCoaching.com). He can be reached at 212.470.6139 or at president@impactfulcoaching.com. 

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