Four steps to help us approach Yom Kippur with the proper mindset, embrace its depth, and carry its spiritual impact into the year ahead

WE

all know Yom Kippur is the holiest day of the year, when we step away from the physical world — refraining from eating, drinking, and all other worldly pursuits. Dressed in white, we resemble malachim, standing in purity before Hashem.

Chazal reveal about this day: “Mi metaher es’chem? Avichem shebaShamayim  — Who purifies you? Your Father in Heaven.” Hashem Himself descends, as it were, to cleanse us, to wash away our stains, and to purify our souls.

Yet many of us find the day challenging. Our eyes drift toward the clock, our fingers riffle restlessly through the machzor… and instead of cherishing Yom Kippur, we dread it. But it doesn’t have to be this way. With intentional preparation, the day can become a deeply moving and uplifting experience.

Here are four steps to help us approach Yom Kippur with the proper mindset, embrace its depth, and carry its spiritual impact into the year ahead.

Step 1:

Preparation — Approaching Yom Kippur Intentionally

Just hearing the words “court case” can make a person shiver. Imagine a person being summoned for even a simple financial dispute. If he were to stroll in unprepared, without reviewing the details of his case or thinking through his defense, we would see him as not just careless but utterly foolish, courting failure with every step.

The days before Yom Kippur are just as vital. A sincere cheshbon hanefesh — an honest accounting of the past year — and seeking forgiveness from others form the “briefing” we need. This does not mean fixing everything at once. Choosing just a few clear areas for improvement gives focus and reality to our teshuvah. Without preparation, Yom Kippur can feel long and heavy; with preparation, it becomes the greatest opportunity of the year.

The Klausenburger Rebbe in the DP Camps

In the dark, desolate days after the Holocaust, the Klausenburger Rebbe ztz”l stood in the Displaced Persons camps on Erev Yom Kippur. Gathered around him were men and women who had lost everything. Many did not even have machzorim.

Yet the Rebbe insisted that everyone sit and prepare before Kol Nidrei. With fatherly patience, he taught them the words of Vidui, explained the tefillos, and urged them to reflect on the year with honesty and courage.

One weary survivor finally voiced the question in so many hearts: “Rebbe, after all that we’ve endured, who has strength left to prepare? And with our broken hearts and souls, do we really need preparation? Can we not simply cry out on Yom Kippur itself?”

The Rebbe’s eyes flashed with a fire that pierced the surrounding brokenness. His voice rang out: “When a soldier goes into the greatest battle of his life, would he dare enter without a weapon? Tonight is the battle of our lives. Preparation is the weapon we carry in our hands!”

Those who were there never forgot what followed. That Kol Nidrei was unlike any other. Survivors who had been robbed of everything stood trembling yet alive, armed with the strength of their preparation of Vidui and tefillah. Their cries tore through the night with such raw intensity that it seemed the heavens themselves had been split open.

On Yom Kippur, we recite the five Shemoneh Esrehs, ten Viduis, and countless stirring Selichos and piyutim. If we do not understand what we are saying, the words can feel long and empty. But if we prepare — if we take time beforehand to learn translations and, more importantly, the deeper meanings — the tefillos come alive.

Today, there is a wealth of excellent English guides to the machzor. Even learning a little in advance can transform the day. Then, instead of watching the clock as a countdown, we savor every moment, hoping the day will linger, immersed in the sweetness of spiritual connection.

Step 2:

Believing in Teshuvah — A New Slate

One of the greatest barriers to teshuvah is not sin itself, but doubt. We ask ourselves: After everything I’ve done, can I really change? Can Hashem truly forgive me?

The answer is a resounding yes. Yom Kippur is Yom Mechilah U’selichah — the Day of Forgiveness. The Navi proclaims: “Im yihiyu chata’eichem ka’shanim, ka’shaleg yalbinu — Even if your sins are like scarlet, they will become white as snow.”

Hashem’s forgiveness is not partial or conditional — it is absolute. He does not leave a shadow of sin behind; He erases it completely.

The yetzer hara taunts us: “You’ve made these promises before. Last year, two years ago — you said the same things, and you failed.” But Hashem, in His endless kindness, cleanses us again and again. In Mussaf we declare: “Maavir ashamoseinu b’chol shanah v’shanah — He removes our sins every single year.”

Rav Aharon Leib and the Shidduch

Shlomo, a fine young man from Bnei Brak, had reached the age of shidduchim. He was a masmid, baal middos, and budding talmid chacham. He met a wonderful girl, and the shidduch seemed perfect.

Just before it was finalized, the girl told him: “I must be honest. As a teenager, I fell terribly — leaving seminary for nearly a year and falling to the lowest levels. But then I made a complete turnaround. I returned to Hashem, rebuilt myself, and since then I’ve grown stronger every day.”

Shlomo was shaken. Unsure, he went to Rav Aharon Leib Steinman for guidance.

After listening to Shlomo’s plight, Rav Aharon Leib asked: “What do you feel?”

“I am iddis, of the finest quality,” he replied. “From a perfect home and background. Why should I settle for less?”

Rav Aharon Leib’s eyes set on the boy. “You are fortunate the girl’s father has not asked me whether to give his daughter to you. I would not allow him to. You do not believe in teshuvah. Do not touch my wine — it may be yayin nesech! This girl has returned with sincerity — she is iddis. And you? You are not even zibburis, the lowest quality.”

The words broke Shlomo, and he wept bitterly. At last he asked, “So Rebbi, what should I do?”

Rav Aharon Leib answered firmly: “If you are asking my advice, go now and close the shidduch tonight.”

Indeed, he followed Rav Steinman’s guidance, and today he is happily married. More than that, he carries a lifetime lesson — a deeper appreciation of just how real and powerful teshuvah truly is.

This is the essence of Yom Kippur. No matter how far we have fallen, no matter how many times we have failed, Hashem erases the past as though it never was. We do not walk away burdened sinners struggling to repair a stained record. We walk away as new creations — cleansed, radiant, and held in the embrace of our Father in Heaven.

Step 3:

Letting Go — Forgiving and Being Forgiven

Chazal teach (Yoma 85b) that Yom Kippur atones only for sins bein adam laMakom — between man and Hashem. For sins bein adam l’chaveiro, we must first seek forgiveness from the person we have wronged.

Equally important is the ability to forgive. “Kol hamaavir al middosav, maavirin lo al kol pesha’av — one who overlooks and forgives others has his own sins forgiven.”

The best preparation may be to identify one person we are truly upset with — the one we feel we cannot forgive — and forgive him.

A Cry in the Shelter

During the terrifying days of the Six Day War, Yerushalayim was under siege. Artillery shells rained down, explosions shook the streets, and in the Mir Yeshivah, bochurim, rebbeim, and neighbors crowded into the underground shelter. Faces were pale, voices trembled, and cries of Shema Yisrael filled the room.

Boom. The walls shook.

Boom. Ceiling tiles fell.

Boom. It felt as if the earth itself was splitting apart.

Amidst the chaos, one voice rose above them all — a woman’s voice, broken and desperate, yet filled with astonishing strength: “Hashem — I forgive him! Ribbono shel Olam, I forgive him! In this zechus, forgive us all! Save us!”

The shelter fell silent.

She cried out again, louder: “For twenty years, he left me an agunah. For years he tormented me, humiliated me — but I forgive him! With all my pain, with all my tears, I forgive him! Please, Hashem, forgive us in this merit!”

Rav Chaim Shmuelevitz, who was present, turned to the bochurim and whispered: “If we survive this war, it will be in her merit.”

And survive they did. When the sirens quieted and the talmidim climbed to the roof, they were stunned. Several shells had landed directly on the building — each powerful enough to level it.

Not a single one had exploded. And everyone knew why.

Step 4:

Carrying Yom Kippur Forward — Lasting Change

On Yom Kippur, we soar to spiritual heights and feel certain that we will walk away transformed forever. But the yetzer hara waits for us the very next morning. That is why the key is not to take on overwhelming kabbalos that quickly collapse, but to choose one small, genuine step forward — a step that can truly reshape our lives.

Equally important is a plan to ensure that step endures. Whether with a small notebook, marking progress on a calendar, or any method that works for us, we must hold ourselves accountable. In this way, Yom Kippur does not fade with Ne’ilah — it becomes the starting point of lasting change, uplifting us not just for a day, but for an entire life.

When we take these four steps and transform our view of Yom Kippur, we come to recognize what a truly astounding gift HaKadosh Baruch Hu has bestowed on us in this day.

Rabbi Yehoshua Frankenhuis is the rav of Kehillas Bnei Aliyah in Ramat Beit Shemesh and mashgiach at Yeshivas Heichal HaTorah. He is a sought-after speaker and the author of several works, including the best-selling Miracle Baby (ArtScroll).

(Originally featured in Mishpacha, Issue 1080)