Photo Credit: Rabbi Naphtali Hoff
Rabbi Naphtali Hoff

In Touched by a Story (ArtScroll Mesorah), Rabbi Yechiel Spiro tells about a young man who was studying in Rabbi Shimshon Pincus’s 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 Hashanah, the rosh yeshiva found Meir sitting despondently in the hallway. Meir told Rav Pincus about his struggles to improve and his continued failures in this regard.

Rav Pincus listened sympathetically. He then recounted to Meir how during the Yom Kippur War he had brought his daughter to Shaare Zedek Hospital in Jerusalem to have a deep cut treated. A soldier was in the emergency room with a gunshot wound to his leg. After completing the surgery to remove the bullet, the operating doctor informed the soldier he was free to return home to recuperate.


The soldier grimaced as he slid off of the operating table. He looked at the doctor and asked incredulously, “Home? You think I’m heading 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 told him 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 beis medrash] 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, Rav Pincus accompanied his student into the beis medrash.

* * * * *

Teshuvah is in the forefront of our minds as we near Yom Kippur, the holiest day of the Jewish year. Our sages tell us that those who seek to engage in teshuvah 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.

The weeks spent reciting Selichos and engaged in introspection helped many of us approach the Day of Atonement with a renewed sense of purpose and an appetite for change, ready to seize the moment and use the incredible gift of Yom Kippur to the fullest degree possible. But there are those of us do not quite feel ready, and we struggle with those “battles” we have lost along the way.

What can we do to ensure that this year’s teshuvah 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 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 us make the most of Yom Kippur.

There are five basic elements of teshuvah: hakaras hachet (recognition of one’s sins as sins), charata (remorse), azivas hachet (“abandoning” or desisting from sin), pei’raon (restitution, where possible), and 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).


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Rabbi Naphtali Hoff, PsyD, is an executive coach and president of Impactful Coaching and Consulting. He can be reached at 212-470-6139 or at [email protected].