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Shiur 3
Teshuvah Means Going in the Right DirectionChapter 1
Standing on the Right Path

Rav Yechezkel Sarna:
“Why Should Teshuvah Make You Sad?”

When I first joined Chevron Yeshiva (5698/1938), I was walking in the hallway of the Yeshiva when Rav Yechezkel Sarna zt”l stopped me and asked, “Why do you look so serious and sad?”

“We are in the middle of the Aseres Yemei Teshuvah,” I answered.

“And who said that we are not supposed to be happy during the Aseres Yemei Teshuvah?” he asked.

“I am trying to do teshuvah,” I explained. “The Rambam writes that real teshuvah is when Hashem can testify on a person’s behalf that he will never return to his sin. Who can hope to reach this level?”

Rav Yechezkel then shouted at me. “Why are you following the stringent opinion of the Rambam? We follow the lenient opinion of Rabbeinu Yonah who has an entirely different interpretation of teshuvah. Rabbeinu Yonah writes that teshuvah means ‘standing on the right path.’ When the Gemara states that Yom Kippur atones for those who repent, it does not refer to those who have already arrived at the destination. It refers to those who are on the right path.”

Rav Yechezkel then added, “Do you know what ‘standing on the right path’ means? I will tell you what I heard from the Alter of Slobodka, who in turn heard it from Rav Yisrael Salanter. He explained it with a parable.”

Rav Yisrael Salanter’s Parable

When Reuven set out from Yerushalayim on the way to Bnei Brak, he asked someone how long the trip would be. “About an hour,” he was told. After traveling for close to two hours and still not having reached his destination, he stopped to ask how far he was from Bnei Brak.

“Bnei Brak? That’s about three hours from here! You’re in the Negev Desert, next to the Ramon Crater.”

“How could that be? When I left Yerushalayim almost two hours ago, they told me Bnei Brak was just an hour away. After traveling for two hours, how could I be three hours from Bnei Brak?”

“Don’t you understand?” asked the person giving directions. “You took a wrong turn and have been traveling away from Bnei Brak all this time, not towards it. You have to turn around now and start driving back to your destination.”

This contains a powerful chiddush! Despite the fact that he is now three times as far from Bnei Brak than he was when he left Yerushalayim, he is actually far better off now than he was then — because now he is going in the right direction. Before he turned around, no matter how close he was, he would never have reached his destination since he was going the wrong way. 

Once he turns in the right direction, it does not matter how far away he is, since he is going the right way. Eventually, he will get to his destination.

“Do you think that in the days between Rosh Hashanah and Yom Kippur a person can achieve complete teshuvah? Do you think that within that time you can change and keep thousands of halachos in Shulchan Aruch?” Rav Yechezkel Sarna asked me. “That is a mistake! Teshuvah takes more time than that. During the Aseres Yemei Teshuvah your obligation is to search for the right direction and position yourself on that path. How long will it take to get there? It could take 120 years. Rabbeinu Yonah is lenient and states that what is required from you is only to position yourself on the right path! So why are you stringent like the Rambam?”

Bachurim must be taught so that it penetrates deeply: the mitzvah of teshuvah is not something to be done in an instant; rather, it is essentially a long process. It makes no difference whether it takes 20 years or 80 years — the mere fact that you are on the right path is what Hashem wants.

Rav Yisrael Salanter inferred this from the wording of the Gemara, which distinguishes between those who are “doing” teshuvah and those who are not (Niddah 70b). The Gemara does not discuss those who have “done” teshuvah, but those who are “doing” teshuvah at the moment. Teshuvah is a long process. We are not expected to complete it instantaneously. “Yom Kippur atones for shavim” (Shevuos 13a). It does not say shavu, those who “did” teshuvah, but shavim — those who are “doing” teshuvah, meaning that they are involved in a process of improvement, even if they have not yet completed it.

People usually have no patience. They expect instant solutions to all their problems. But we need to know and internalize that we are built in such a way that change takes time. We shouldn’t be in a haste or hurried — the main thing is to be going in the right direction.

For example, if a person makes a Rosh Hashanah resolution to refrain from talking lashon ha’ra, he cannot expect to change his speaking habits instantly. If he commits to learning the sefer Shemiras HaLashon once over the course of the year, he is “standing on the right path,” since that is where the path starts. If he keeps on going, eventually he will reach his destination and stop talking lashon ha’ra entirely.

Compiler’s note: 

I heard this principle of “standing on the right path” from Rav Shlomo dozens of times regarding any struggle in avodas Hashem. Rav Shlomo would calm the person and say, “Who asked you to change in one moment — that in one moment you should take control and reach the highest level? The main thing is the path. Even if it takes you 80 years, you are already ‘standing on the right path,’ and that’s what matters.”

Rav Shlomo used to say: “You are young, and you want everything to come quickly. It takes a long time to understand the yetzer, to understand one’s impulses, and to figure out how to cope with the yetzer.”

Rav Isaac Sher once told me that for sixty years he had been struggling to improve his middos, until finally, in his old age, he began devoting the majority of his time towards this task. Middos cannot be changed in one day. Self-control cannot be achieved in one fell swoop. The main thing is to be in a state of “doing teshuvah.” The Gemara (Shevuos 13a) says that Yom Kippur atones for those who are doing teshuvah (shavim); it does not require one to have completed teshuvah (shavu).

This is the optimistic view of teshuvah that HaKadosh Baruch Hu revealed. The sinner need not suffer or die for his sins. He can do teshuvah and be forgiven. This might take many years, but just by setting one’s feet upon the path, one fulfills the mitzvah of teshuvah.

In the course of my years in Chevron Yeshiva, Rav Yechezkel would often give shiurim during the month of Elul, in which he developed this point and clarified that the halachah in this regard follows Rabbeinu Yonah, and not the Rambam. Rav Yechezkel based himself on the mesorah that he received from the Alter, who received it from Rav Yisrael Salanter, as it is explained at the end of ma’amar 30 of Ohr Yisrael.

Recognizing Our Misdeeds
as the Beginning of Teshuvah

I have often advised learning the end of ma’amar 30 of Ohr Yisrael. There, Rav Yisrael Salanter deduces from the language of the Gemara (Niddah 70b), “Here is where they are doing (osin) teshuvah,” that they do not need to have completed teshuvah (asu), but just have started the process. He explains that the judgment between life and death on Rosh Hashanah depends on a person’s recognition of his shortcomings without rationalizing and making excuses for his behavior. He describes this recognition as “much’shar l’teshuvah,” meaning prepared to do teshuvah. As long as a person is aware of his faults and is concerned about them, there is a good chance that he will eventually do teshuvah for them. In such a case, Hashem waits patiently for him to return. But if he has no such recognition, then what hope does he have of ever doing teshuvah?

Chovos HaLevavos (Shaar HaTeshuvah 2) calls this to “clearly recognize the shamefulness of his deed.” Even if a person does not yet know how to overcome his bad traits and keeps doing those bad deeds, just recognizing that they are wrong is the first step towards teshuvah. This is enough to classify a person as “doing teshuvah.” It is the first step on a path that can very well take one’s entire life to travel.

Advice for a Yeshiva Bachur Who Stumbled


A yeshiva bachur stumbled into a terrible sin. Afterwards he felt very broken about it. What can I say to encourage him?


The first thing is to show him the text of Chovos HaLevavos, which states that teshuvah begins with “clearly recognizing the shamefulness of his deed.” The very fact that he feels bad about his mistake shows that he is already on the path of teshuvah. Turn this feeling into an elevating experience — that being on the path to teshuvah already qualifies him for atonement on Yom Kippur. Way before he has started doing anything concrete to rectify himself, the fact that he knows and understands that he did something wrong is the beginning. It is enough to be considered in the category of “doing teshuvah.”

Help him realize that teshuvah is a long road, which he has already begun to travel. Realizing that something is wrong is the first step, which comes long before the mistake can actually be corrected. He has already satisfied Rav Yisrael Salanter’s definition of teshuvah, after which Hashem is patient and awaits his return in good time.

He should recognize that most people sin without remorse. If he feels remorse and is upset with himself, this shows that he is already on a high spiritual level, which is beloved to Hashem.

You will have a hard time convincing him of this, since he is probably used to hearing people say that anyone who did what he has done is sinful and wicked. He is not used to hearing about the positive side of teshuvah, and will probably not know how to see things this way.

He might think that you don’t understand, or that you are just making things up to calm him. That is why it is best just to show him the text of the Chovos HaLevavos, and ask him what he thinks it means. 

The first thing is for a person to clearly recognize the shamefulness of his deed. If this is not clear to him, if he is uncertain about it or if he excuses himself by saying it was just an accident, he can never feel remorseful about it. 

(Chovos HaLevavos, Shaar HaTeshuvah 3)

Many people are unwilling to admit their mistakes. They are so uncomfortable about feeling guilty that they justify themselves with any excuse, or at best claim that it was not their fault since it was an accident. Such people have no hope of ever changing. They will repeat their misdeeds again and again for the rest of their lives, and will never even set foot on the path of teshuvah.

That is why the Chovos HaLevavos calls “clearly recognizing the shamefulness of his deed” the first step of teshuvah. This means facing ourselves, to recognize the negative traits that we tend to ignore.

The Chovos HaLevavos implies that clarity is the first step, which comes even before remorse. Once a person sets aside all his excuses and admits that there is a problem, he has begun to unravel the solution. The second step of remorse will automatically come in turn, and he will then proceed step by step down the path of teshuvah.

That is how a person who is overcome with guilt should be guided towards feeling good about himself. Even if he knows that he has not yet gained control of himself and will probably sin again, he is already on the path of teshuvah. He should be encouraged to cherish the remorse within himself and guard it from becoming extinguished. Rather than becoming so steeped in sin that he no longer cares, he should leverage his guilt to his advantage as a catalyst for change.

Try to impress upon him that teshuvah is a complex sugya which must be studied in depth, so as to understand the steps that must be taken one after another in order to walk slowly and steadily down the path. He must learn all the stages of how to progress and what is expected of him according to his strengths and abilities. There is no reason to feel broken. Little by little, step by step, he will eventually overcome and achieve self-control.

I have often discussed this with educators, who seemed skeptical about it. After I showed them the Chovos HaLevavos inside, they started to wonder if perhaps I might be right. Rav Yisrael Salanter describes at length this principle of just recognizing our mistakes in order to merit life in the judgment of Rosh Hashanah and Yom Kippur. Without having first seen the Chovos HaLevavos, it is hard to understand how Rav Yisrael reached this conclusion.

Teshuvah is a sugya in the Talmud, which must be learned b’iyun like any other important sugya, in which each word is analyzed from a dozen angles and discussed and debated until clarity is achieved. Otherwise we will approach teshuvah with our notions that were never checked for accuracy.

Three Tools for Success

When it comes to guiding talmidim on the road to success, the following three principles must be taught.

1. Believing in Change

Often a person becomes stuck with the feeling that he is unable to change. “This is how I was born. It is my nature to be that way. How can I change it?” he thinks to himself, or, “That is the kind of house I was raised in. That is how all my friends act. How can I act any differently?”

An educator needs to find a way to help his talmidim believe in their power to change. Sometimes this can be done by pointing to the example of others, who also thought that they were stuck in a rut and could never change, but still managed to overcome and improve themselves. Sometimes the talmid’s own experiences can be used, in which he managed — not necessarily in matters of Torah observance — to change his habits in a way that he had previously thought impossible. This is the first important principle of growth — belief in the power to change.

There are three basic reasons why people think they are unable to change: imagination, fear, and habit.

Imagination: This is one of the most powerful influences on a person’s behavior. A person might imagine that he can do things that are really far beyond his powers; and to the contrary, he might also imagine himself incapable of achievements that are really within his reach. If he were just to recognize the true extent of his abilities, he could change quickly and achieve great success. The problem is that his delusions prevent him from advancing, leaving him stuck in his current state.

Fear: Some people are scared of change. They prefer to remain with the current situation, despite all its problems, rather than face the unknown. The truth, however, is that as a person gets used to making changes, his self-confidence grows. One acquires the ability to effect positive change through tikun ha’yetzer — “fixing” his yetzer of fear.

Habit: The more that a person gets used to a certain mode of behavior, the harder it is for him to change. Rabbeinu Yonah explains (Shaarei Teshuvah 1:5) that this is one of the reasons that Chazal encourage us to pursue teshuvah immediately, and not postpone it. The more we postpone teshuvah, the more entrenched we become in our bad habits until they become second nature, at which point it is harder to change.

Yet the truth is that we have the power to drop our bad habits and change our behavior. This is one of the foundations of free choice, upon which Torah observance is based. Just as a person can choose between good and evil, between right and wrong, so too can he choose between remaining stagnant and improving. There is no excuse for saying, “It’s not my fault. This is who I am. I cannot change.”

It is within the power of every person to choose his own path in life. A person’s conviction that he is unable to change is simply a product of his imagination, which he should — in his own best interest — set aside.

2. Setting Realistic Goals

Sometimes a bachur tries to reach for a goal that is beyond his ability, and gets frustrated when he fails. Throughout his writings, the Vilna Gaon warns that a person must not leap too far ahead. When helping a talmid develop plans and goals for advancing in Torah study or any other spiritual endeavor, it is important to make sure that the plan involves a steady, gradual ascent that is within his abilities. The Gaon writes:

“The swift of foot is sinful” (Mishlei 19:2). When a person gets used to a good habit, it becomes second nature to him. However, he must advance in character growth one step after another, like climbing a ladder, and not jump up to a rung that is too high for him. In this sense, “the swift of foot” who hurries up to a level that is too high for him “is sinful.” He will lose all he has attained because he will fall. 

(Vilna Gaon on Mishlei 19:2)

The Vilna Gaon uses a ladder as a comparison. One who tries to jump to a high rung will fall — and break his head! Likewise, a person who tries to rise too high, too fast, is destined to come crashing down. Despite his good intentions, he is considered “sinful,” since he set himself on a course that is doomed for failure. When he fails, not only will he lose the higher rung that he tried to achieve, he will lose everything that he has attained up until now too, since he will become too frustrated and upset with himself to continue functioning normally. For example, an ambitious talmid sets a goal at the beginning of a winter zeman to complete the masechta by Chanukah. By Rosh Chodesh Kislev he realizes that his goal is impossible. He becomes frustrated with himself and broken.

His breaking point was not on Rosh Chodesh Kislev when the truth finally set in. His breaking point was at the beginning of the zeman, when he set an unrealistic goal for himself. The Vilna Gaon calls this a sin, since by setting for himself an unachievable goal, he has done the opposite of “standing on the right path.” He chose the wrong path — the path that can only lead to failure.

When a person makes a realistic goal for himself, then every small step he takes brings him closer to success. But when the goal was never possible in the first place, then he was going in the wrong direction from the very beginning.

The Vilna Gaon thus explains the subsequent verse, “Man’s foolishness makes him slip on his path, and his heart grows angry at Hashem” (Mishlei 19:3). People make foolish decisions, pay the price for them, and then get angry at Hashem for their failures.

Chazal assure us that “when a person comes to purify himself, he is granted assistance.” Sometimes a person starts learning Torah or doing mitzvos, and then stops because he finds it too difficult. He gets angry at Hashem, since he does not see the assistance that he was promised.

In truth, it was due to his own foolishness that he was denied this help, since he should have gone according to his level, one step after another, and not leaped towards a level that was too far above him, as we wrote above.

Had he gone on the path that was right for him, he would have proceeded safely and received the assistance he needed. But instead he went foolishly without presence of mind; he never even set foot upon the path that was right for him. Therefore he received no help. 

(Vilna Gaon on Mishlei)

For this reason, it is so important to progress slowly, and not try to achieve too much at once. By progressing at the right pace, with perseverance, he will eventually reach his destination. In the meantime, Yom Kippur atones even though he has not yet reached his goal, since he is advancing in the right direction towards success.

3. Learning to Enjoy Hard Work

One of the most important factors in achieving success in one’s hard work is learning how to enjoy the hard work. This involves enjoying the work itself, and also enjoying the sense of accomplishment that comes when a person achieves something he worked hard for.

Enjoying the work itself: People sometimes think that work and enjoyment are mutually exclusive, but this is not true. Despite the fact that the simple connotation of work implies difficulty, nevertheless, the work itself provides a person with enjoyment. The Vilna Gaon explains that the verse, “A happy heart betters the face” (Mishlei 15:13), refers to those who are happy in their hard work. Enjoying hard work and being happy in one’s effort brings a sense of satisfaction, which encourages a person to continue working harder.

Elsewhere (Mishlei 2:14), the Gaon explains that joy comes at the moment of “chiddush.” When a person works towards something new, the moment he achieves it is a moment of joy. This creates a cycle in which his joy encourages him to strive farther, where his new achievements will bring him further joy. In this cycle, the hard work itself becomes part of the joy.

Talmidim must therefore be trained to want not only the results of their hard work, but the hard work itself. They must be encouraged to overcome the natural inclination towards laziness, and press themselves to understand difficult sugyos, without taking any shortcuts — because the greatest satisfaction and enjoyment lie within the hard work itself.

Furthermore, whereas in the world of employment, people are rewarded for results, in the world of Torah and mitzvos we are rewarded for the hard work we invested. As Chazal say in Avos (5:22), “Lefum tza’ara agra — according to the hardship, so is the reward.”

If two shoemakers make shoes of identical quality, one cannot charge more than the other just because it was harder for him or took him longer to make it. People pay for results, not for work. 

In Torah and mitzvos the opposite is true. Hashem rewards us for our hard work. Therefore, the more an educator succeeds in causing his talmidim to enjoy the path itself, and not just the destination, the more likely they are to stay on the right path.

Sense of accomplishment: There are two ways to confront the yetzer ha’ra. One is to fight and conquer our urges, and the other is to “correct” our urges through satisfaction in learning Torah and serving Hashem. It is best to train young people using mainly the second method, with happiness and enjoyment. Rav Yisrael Salanter (Ohr Yisrael, 30) applies to this the verse, “Rejoice, young man, in your youth” (Koheles 11:9).

Therefore it is very important that their hard work should be with joy and enjoyment, and not just by forcing themselves. The Vilna Gaon warns that if one keeps trying to force his yetzer, he will eventually break. Only by finding satisfaction and enjoyment in his avodah can a person continue onwards. For example, the talmid should always be helped to find the sweetness of Torah in his learning; otherwise, he will not endure.

People abandon Torah study for one of three reasons. The first is that they have been seduced by their yetzer ha’ra to chase after the pleasures of this world, under the impression that these pleasures are the real good and will always last.

The second is that they would rather waste their time in idle chatter. Although this cannot even be considered a pleasure of this world, even so, they find it sweet.

The third is that they find Torah study too hard. They want Torah to come to them by itself, without hard work. When it does not come and they sense no enjoyment from it, they abandon it, for they do not experience its sweetness. 

(Vilna Gaon on Mishlei, 1:22)

For more from Rav Hoffman….

Read and discover… the Secrets of the Soul

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