A Comprehensive Program to Maximize The High Holy Days

Category: Yom Kippur

6.01 The Ten Days of Teshuvah: The Meaning of the Al Chet Confession



When one begins to look at the task of teshuva, it can be overwhelming. We have done so many things wrong over the past year that it is hard to know where to begin. Do we take out a list of the Taryag Mitzvos and ask, what were all my transgressions on mitzvah number 1, and number 2 etc.?” That doesn’t seem to be the direction to go in, for it would be very time consuming and very draining.

The answer is much simpler. We must come up with a plan for spiritual growth that, in the future, will lead us to abandoning our transgressions. If we could find the central roots of our transgressions and attack them had on, eventually, most of our transgressions would fall away. That is the goal of the Teshuva process.

This is the secret of the “Al Chet” confession that we say so many times on Yom Kippur. R. Dessler (zt”l), in his famous work, Miktav M’Eliahu. points out that the Al Chet confession is not a list of sins, per se, but rather it is a list of the roots of sins. Each one of the sins that are listed is a root cause for sin and, therefore, if you look carefully at the list it might be quite helpful in figuring out what the central problem is that is dragging you down.

Therefore, before Yom Kippur arrives, it is very important to sit down and learn what the Al Chet Confession is and make it relevant. In it is the answer to what might be holding us back from greatness. The following presentation is a questionnaire designed to help you find out which are the areas that you need to be working on.

After you have gone through the transgressions listed and have found areas of weakness, make your plan on these areas. But please remember, change is a process that doesn’t happen immediately. Don’t choose too many things to work on in your plan. It might just be too overwhelming. (Please see sheet numbers 12 and 15 for further information).

1.For the sin that we committed before You under duress and willingly.

Explanation of under duress – These are the sins that you committed because you thought you were not in control, but you really were, on a certain level. If you had not put yourself into compromising situations, or even if you had, but had taken the trouble to make fences, you would not have committed the transgressions you did.

Did I put myself into compromising situations and then when I transgressed said it was accidental?
Did I rationalize that had no choice but I really did? (e.g. you davened in a fast minyan and then xxcomplained that you had no cavanah, or you spent time with people who speak loshon hara and then xxcomplained that you ended up speaking it, etc.)
Did I make “fences” so that I won’t transgress?
Do I have a penalty system set up so that I won’t do certain sins?
Even if something did happen to me that was not in my control, did I ask “why did G-d do this to me”?

Willingly – Did you sin because you wanted to indulge in a pleasure?

2.For the sin that we committed before You through having a hard heart

Did I ignore the poor and the weak?
Did I ignore helping people who are not frum? Did I pay attention to their pain?
Was I kind, compassionate and loving when I needed to be?
Do I feel the pain of the Jewish Nation?
Did I give charity to the poor in a cold way?

3.For the sin we committed before You without thinking (or without knowledge)

Do I act like a judge in all my dealings with the world, weighing out what is right and what is wrong?
Do I remind myself constantly of the major goals of my life?
Do I consciously involve G-d in my life?
Am I learned in halacha?
Do I have a goal to be a thinking individual?

4.For the sin that we committed before You through the things we blurted out with our lips.

Do I think before I speak?
Do I often make hasty outbursts?
Do I often make hasty vows or oaths?
Do I often make hasty promises?

5.For the sin that we committed before You in public and in private

Sins In public – Did I do foolish or sinful things to attract attention or approval?
Did I do mitzvos in public, that if I was in private I would not have done them?
Was I modest with my accomplishments?

Sins in private – Do I reassure myself that since no one sees I am free to sin?
Have I denied that G-d exists because of the sins that I did in private?
Do I realize that doing sins in private, in many ways, harms my relationship with G-d in a more serious xxway than doing them in public?
When I was alone did I realize that Hashem was alone with me?

6.For the sin that we committed before You through immorality

Did I have any improper thoughts?
Did I look at anyone that I shouldn’t have?
Did I talk to anyone that I shouldn’t have?
Did I tell any improper jokes?
Do I realize immorality is a major obstacle to
achieving closeness with G-d?

7.For the sin that we committed before You through harsh speech

Did I speak to anyone in a harsh and forceful manner?
Did I express my opinions in a too forceful, non-holy manner?
Did I speak in a soft spoken, sensitive manner when it was necessary?

8.For the sin that we committed before You with knowledge and deceit

Did I use knowledge in a deceitful way?
Did I use knowledge to deceive others?
Did I use knowledge to deceive myself (i.e. did I rationalize sins in order to do what I wanted to)?
Did I use knowledge to circumvent the spirit of the law?
Did I show off with my knowledge of the Torah in order to impress others?

9.For the sin that we committed before You through inner thoughts.

Did I think in a negative way about people?
Did I fantasize about doing sin?
Did I think about G-d in my deepest emotions?

10.For the sin that we committed before You through wronging a friend

Did I defraud my friends?
Did I wrong friends by hurting their feelings?
Did I take advantage of my friends even though they trusted me?

11.For the sin that we committed before You through insincere confession

When I confessed to G-d on Yom Kippur did I do so with sincerity and honesty?
Did I keep my commitments that I made in my confessions to G-d?
Do I realize that keeping my commitments to G-d will lead to self-respect?
Do I confess to G-d when I do something wrong?

12.For the sin that we committed before You while in a gathering of people dedicated to negative things.

Was I in any gathering that led to discussions of negative things?
Was I in any gathering that led to negative activities?
Did I associate with moral and ethical people?
Are you looking to associate with the proper people?

13.For the sin that we committed before You willfully and unintentionally.

Did I sin out of a desire to demonstrate my independence of G-d’s authority (G-d forbid)?

Did I sin in an unintentional way that had an aspect of carelessness to it?
Could it have been avoided? Could I have taken the proper precautions to avoid doing that sin xxunintentionally?

14.For the sin that we committed before You by degrading our parents and teachers

Did I have contempt for my parents in my mind?
Did I verbally express my contempt?
Do I realize how much they have done for me?
Do I respect my parents?

Do I realize that the way to wisdom is to respect teachers and as a result receive the transmission of the xxTorah?
Do I respect my teachers?
Do I appreciate my teachers for all the good that they have done for me?

15.For the sin that we committed before You by exercising power

Did I sin by taking advantage of the weak?
Do I realize that it is not the Jewish way to throw your weight around?
Did I force someone to do something against his will?

16.For the sin that we committed before You through desecrating G-d’s name

Did I give a bad impression of being a religious Jew to someone and therefore desecrated G-d’s xxname?
Did I misuse my power as a role model by sinning or doing something that I shouldn’t be doing?
Did I smile to people?
Was I dressed properly?

17.For the sin that we committed before You with foolish speech

Did I sin by talking about stupid things?
Do understand that speaking words of Torah is the way to become a great person?
Do I associate with people who speak words of Torah in their spare time?

18.For the sin that we committed before You with vulgar speech

Did I sin by contaminating my mouth with vulgar speech?
Did I sin by hearing it?
Did I protest when I heard it?
Did I always express myself in the holiest and most pleasant way possible?

19.For the sin that we committed before You with the yetzer hara (evil inclination)

Have I incited my lusts and my urges?
Have I put myself into situations that do this?
Have I used the tools and techniques that I know are able to control my yetzer hara?

20.For the sin that we committed before You against those who know and those that did not know

Have I wronged people to their faces?
Have I wronged people behind their backs?

21.For the sin that we committed before You through bribery

Have I been influenced or bribed to do sins because of flattery?
Have I been influenced or bribed to do sins because of favors?
Have I been influenced or bribed to do sins because of money?
Do I realize that money is the biggest pull on one’s honesty and integrity?
When didn’t you do the right thing because you wanted approval?

22.For the sin that we committed before You through denial and false promises

Have I sinned through denial of the truth to others?
Have I sinned through denial of the truth to myself?
Have I sinned through false promises?
Did I say any untruth in the slightest way?
Do I realize that the mark of a great man is that he is as meticulous about truth as possible?

23.For the sin that we committed before You through Loshon Hara (negative speech)

Have I spoken Loshon Hara?
Do I know the laws of Loshon Hara?
Do I know the laws well?
Did I try to avoid talking about people as much as possible?
Do I realize that this is one of the keys to the redemption?

24.For the sin that we committed before You through being scornful (or scoffing)

Did I ridicule serious things?
Did I scoff at true concepts?
Did I mock someone who tried to criticize me?

25.For the sin that we committed before You in business

Have I been scrupulously honest in every financial transaction that I made?
Do I realize that this area is what usually ruins people’s integrity more than any other?
Do I realize that integrity is the mark of every great man?
When I was successful in business did I give G-d credit for the success?

26.For the sin that we committed before You with food and drink

When I ate, did I let the animalistic part of myself take control?
Have I spoken words of Torah at the table?
Have I sinned by not keeping kashrus properly?
Did I have gratitude to G-d for providing me with food?
Have I said blessings over food properly?
Have I wasted food?
Have I eaten unhealthy foods?

27.For the sin that we committed before You with different types of monetary interest

Do I know the Torah laws on taking interest?
Have I taken or given any loans with interest without a heter iska (a special contract that permits interest xxtransactions)
Have I made a profit as a result of someone else’s misfortune or downfall?
Am I greedy?
Am I stingy?

28.For the sin that we committed before You by having an outstretched neck (with head held high)

Have I shown arrogance through body language?
Do I walk in a humble manner?
Do I present myself in a humble manner?

29.For the sin that we committed before You with eye movements

Did I look at someone in a flirtatious way?
Did I wink at someone who I should not have?
Did I “express” loshon hara with eye movements?
Did I stare impolitely at someone?
Did I look at people doing mitzvos?
Did I look at the righteous people?

30.For the sin that we committed before You by endlessly babbling

Do I tend to have conversations with no meaningful content?
Do I tend to sound like a chatterbox?
Do I concentrate on what I say?
Do I say brachos properly?
Do I say prayers properly?

31.For the sin that we committed before You with haughty eyes

Did I look at people with an inner feeling of superiority?
Did I love each Jew with warm and loving eyes?

32.For the sin that we committed before You with a strong forehead (you were brazen)

Do I have the Jewish attribute of shame?
Have I lacked the attribute of shame?
Do I stand before G-d in shame?

33.For the sin that we committed before You in throwing off the yoke

Have I accepted the responsibility for doing all of the mitzvos?
Have I accepted the responsibility of living with G-g?
Have I accepted the responsibility of learning Torah when I should be?
Do I love all Jews?
Am I a responsible person?
Do I keep my commitments?
Am I lazy?

34.For the sin that we committed before You in judgement

Have I judged G-d unfairly?
Have I judged people unfairly?
Have I made an effort to judge people positively?
Can I judge truth properly?

35.For the sin that we committed before You entrapping a friend

Have I taken advantage of family and friends and put them in a situation where they couldn’t say no to xxdoing you a favor?
Have I manipulated family and friends? Have I violated the trust of people who have confidence in me?
Did I entrap a friend to do averas with me?

36.For the sin that we committed before You through a begrudging eye

Was I stingy?
Was I jealous?
Did I find ways not to give tzedaka?
Was I unwilling to do favors when I should have?
Do I think about other people as well as myself?

37.For the sin that we committed before You through light-headedness

Do I walk around as if the Al-mighty is standing right before me?
Do I behave properly in the Beis Midrash?
Do I behave properly in the Beis Knesset?
Do I behave properly at the Kosel?
Do I talk about proper things in the above places?
Did I have excessive levity?
Do I treat religious books with the proper respect?

38.For the sin that we committed before You by being stiff-necked?

Am I unreasonably stubborn?
Do I think that I am always right?
Have I been single-minded and lost my objectivity when I really wanted something?

39.For the sin that we committed before You by running to do evil?

Have I hurried to commit sins?
Was I motivated to do averas?
Do I walk in the proper way?
Did I slow down to say brachos and daven?
Do I run to do mitzvos?
Do I run to the Beis Knesset?

40.For the sin that we committed before You through telling people what others said about them

Have I turned people against each other?
Do I know the laws against richilus?
Do I realize that richilus can destroy a society?

41.For the sin that we committed before You through vain oath taking

Have I sworn oaths in vain?
Have I sworn falsely?
Did I use G-d’s name in trivial ways?
Do I realize how careful I must be with Hashem’s name?

42.For the sin that we committed before You through baseless hatred

Have I hated people, on a personal level, instead of disagreeing on issues?
Have I hated people instead of their evil deeds?
Do I realize that when people sin it is mostly because of confusion and weakness?

43.For the sin that we committed before You in the matter of extending the hand

Have I put forth my hand to help people?
Have I joined hands with wicked people?
Have I stretched forth my hand to the poor and the needy?

44.For the sin that we committed before You through confusion of the heart

Have I not gotten the answer I needed because of laziness?
Have I not worked out issues because of laziness?
Have I not gotten the answer that I needed because I did not want to get the answer?
Do I know what I am living for?
Do I have proper goals?


After you have gone through the list and you find areas of weakness, these are the areas to make your plan on. But please remember, don’t make your plan on every single area of difficulty. Choose the areas that will be the most effective in solving your other problems. Change is a process that doesn’t happen immediately. Don’t choose too many things to work on in your plan. It might just be too overwhelming. (Please see sheets number 12 and 15 for further information on the rate of change and how to do teshuvah). By choosing the areas that are the root problems this will. allow for the greatest success in the teshuva process.


Yom Kippur is tomorrow night. The day we have been preparing for is now just around the corner. It is very important to finalize and complete all your preparations in these last few hours left.* One who has prepared well will now taste the fruits of his labors on Yom Kippur.

One who studies Torah in order to teach, Is given the means to study and to teach; and one who studies in order to practice, Is given the means to study and to teach, to observe, and to practice (Perkl Avos 4.6).

This concludes the High Holy Day series. I hope that it has proven helpful in increasing the awareness of the ideas needed to make these important days meaningful and procluctive. Gmar Chasima Tova.

* Even on Yom Kippur itself progress can still be made, even from scratch. But we all know that it would be foolish and reckless to count on this.

5.02 The Ten Days of Teshuvah; Restoring Your Lost Innocence



We are now four days into the Ten Days of Teshuva. The obvious priority for these days is teshuva. There is no greater opportunity to get close to G-d, than the next six days of the year. The time for preparation is over. The time for teshuva is now. The most important question to ask at this time is how much teshuva have you done over the past few days?And if the answer is not as much as you should, then now is the time to change.


The Gemora points out a fascinating aspect of human psychology:

R. Huna said, ‘Once a man does wrong and repeats it, it is permitted to him.
“It is permitted to him!” Can you really think such a thing?
Rather it becomes to him as if it is permitted. (Kiddushin 40a)

When a man does a transgression and then he does it again, it no longer appears to him as a transgression. It becomes as if it is permitted. As a matter of fact, the Baali Mussar (Masters of Self-Perfection) point out that the third time you do it, not only does it become as if it is permitted to him, but it-even becomes a mitzvah!

People lose spiritual sensitivities by repeating a transgression. A holocaust survivor was once heard saying, ‘The first time I ate treif (non-kosher food), I thought I was going to die; the second time, I felt a little pain; and the third time, something snapped and I didn’t feel any guilt.”

The school of R. Yishmael taught: Sin dulls the heart of man, as It is said: Neither shall you make yourselves unclean with them, that you should be defiled thereby (Vayikra 11.43). Do not read ve-nitmasem (that you should be unclean) but u-netmosem (that you should become dull-hearted).n (Yoma 39a)

The blunting of man’s finer perceptions which make him unable to distinguish between right and wrong is the outcome of continual sin. This spiritual insensitivity will not only lead you to transgress in the future, but it will remove you from G-d in a very deep way.

When a person does teshuva the reverse occurs. Teshuva sharpens your spiritual nerves. You are now saying to G-d, “I feel it is wrong. I feel regret.” You restore your spiritual being back to sensitivity. To give you an example of spiritual sensitivity imagine this: the Chofetz Chaim fainted when he first saw a Jew driving on Shabbos.

During this very important time period this is exactly what we have to do. Our goal is to try to resensitize ourselves away from sin. The purpose of this sheet is to try to awaken some of the old sensitivities that we might have lost over the past few years, while we were pushing ahead in other areas of our lives.

We must resensitize ourselves to the time prior to when we committed that first transgression. This restoration of innocence is hard work but a very necessary and productive step during the Ten Days of Teshuva.



Remember many years ago you walked into the yeshiva and you heard that there was a mitzvah not to speak Loshon Hara? You were fascinated. You thought to yourself, ‘What an amazing thing. I am going to learn those laws. You found a copy of Guard Your Tongue, and you spent a whole day learning the laws. For the next week, you were a changed person. Every word out of your mouth was carefully weighed out and measured. But then something happened. You noticed that other people were not so particular as you. As a matter of fact, when you were very careful, you made people nervous. So, for whatever reason, you stopped being so careful. You wanted to be more “normal’ and accepted. After all, who were you to be acting so frum anyway?

Now, it is many years later, and you look back when you were a “new guy in the beginners program” with a little envy. Why not try to catch a little bit of the old spirit and get back these old sensitivities?


If you could go back and do it all again, what would you do differently? You have probably learned a lot about yourself these past few years. You have missed a few things along the way that are probably difficult to go back and get. And why is it difficult? Because you think you are so far along in the process that it is an embarrassment to go back and learn it.

So what if you have been here for four years and still don’t understand fully what is written in the siddur. That shouldn’t hold you back from still learning it. Maybe you realize that you don’t understand at all the meanings behind the main holidays. So why not go back and get it now?

Try this exercise. Imagine in your mind’s eye that you are arriving at the yeshiva today for the first time as the person you are, at the level you are on now, and no one knows you and you have never been in any classes in the yeshiva. You now have the opportunity to set up any schedule that you want. What would you do differently? What changes would you make in your life, if no one knew you?

The purpose of this exercise is to focus a person on that part of himself that might have gotten lost over the years. Many people subconsciously judge themselves by the number of years that they are observant. This unfortunately causes a person who needs to go back and learn something he missed to not do so for fear of being embarrassed. As a result he might lose touch with certain essential ingredients that are needed to make up the recipe of his personality.

So ask yourself. How would I start from scratch if nobody knew me? This might bring you to startling realizations about certain areas that might need correcting because you have lost touch with the deepest parts of your soul.


At one of the branches of Aish HaTorah in America, I witnessed the following story:

There was a man who wanted to get ahead in life. One of the things that he felt was holding him back was the fact that he was Jewish. So he decided to run away from his Jewishness. He went to Iowa, changed his name, and disappeared into the heart of Christian America.

There was a woman, whose Jewish mother intermarried into a “fine” Baptist family. She was raised as a “fine” Christian girl in the heart of Iowa. One day, this “escaping’ Jew met this “fine” Christian girl and they were married. They had a daughter who they raised as a non-Jew.

The daughter grew up, left Iowa and moved to the “Big City” where she got a job as a secretary for an organization called “Aish HaTorah.” During this time period, for the first time, her father revealed to her mother that he was Jewish. He expected his wife to be angry, but instead she replied, “Oh, my mother was Jewish also.” They both laughed at the irony of the whole situation.

That day the father spoke to his daughter. He told his daughter the story in a laughing way. “Do you know that according to Jewish law you are considered to be a full fledged Jew? Now isn’t that the funniest thing you ever heard?” The girl didn’t laugh. She was extremely impressed with the people at Aish HaTorah and could not understand why she felt so connected to what they were doing.

That night she went to daven for the first time. It was Friday night. I saw her bewildered expression when she left the Beit Knesset for the first time in her life after having found out she was Jewish. She said the following, “How can it be in a place of G-d, people don’t pay attention during their prayers to G-d? Don’t they realize they are talking to G-d? Is there something I don’t understand here? There were even people talking about business.”

Remember the first time you prayed in your life? Do you remember the anticipation? Do you remember how you closed your eyes and spoke to G-d from the depths of your heart? Do you remember how shocked you were when you saw people not acting in a proper way during the service? Are we these same people many years later?

If we daven three times a day for a year, that is over 1000 Shemoneh Esreis. How many Shemoneh Esreis have you prayed so far? 5000? 10,000? Now remember how hard you tried to concentrate during Shemoneh Esrei #1-10?

Take one prayer and pretend it is the very beginning. Put yourself back into those first few days of prayer and just let go. You might find it to be a very powerful experience.



Here you are in the Ten Days of Teshuva and the tension is on. And you so badly want to figure out a way to open up your heart. But you just don’t know how to do it. Feel the pain of how far you are away from G-d. Feel how close you want to be.

The Gemora in Brachos (16a) talks about the different prayers that the Rabbis used to say at the end of the Amidah prayer. One of the prayers mentioned there adequately expresses this frustration : Sovereign of the Universe, it is revealed and known to You that our will is to perform Your will, and what prevents us? The yeast in the dough and the subjugation to the foreign powers. May it be Your will to deliver us from their hand, so that we may return to perform the statutes of Your will with a full heart.

The yeast in the dough symbolizes the Yetzer Hara (evil impulse) which causes negativity to ferment in our heart. The subjugation to the foreign powers symbolizes the exile with its attendant value system and social pressures to “conform,” which drain our energy and ability to serve G-d.

The message of the prayer is a powerful one. We are saying, G-d, we totally want to be with You. But the Yetzer Hara and the exile just drain and sap our energy. Help us out so we can return to You. This is our deepest desire.

One way to bring us back to a state of sensitivity to sin is to express our deepest desire not to be in sin. At the end of the Shmoneh Esrei prayer, cry out to G-d (in a quiet voice, of course) that your deepest desire is not to be in sin. This is a tremendous form of teshuva in and of itself.


One of the meanings behind the blowing of the Shofar is to precisely give us this message. Deep down in the bottom of our soul there is a pure part that is smothered by all the insanities of the day. That part is blocked out by our Yetzer Hara. When the Shofar is blown on Rosh HaShanah, the Yetzer Hara is confused. That gives us an opportunity to get in touch with the deepest parts of our essence that we do not have the ability to reach during the year.

It is precisely at that moment, when the Shofar is blown, that people are known to cry out to G-d from the bottom of their soul, “G-d, You are all that we want.’ It is exactly at that time, when their souls are exposed to the Al-mighty without any barriers, that they let go. (It is interesting to note that the Shofar is blown with different types of sounds to symbolize the different ways that a Jew cries. This is to show us that our heart should cry out to G-d when the Shofar is blown no matter who we are or what situation we are in.)



One of the ways to get back a lost sensitivity to sin is to watch an expert at a certain mitzvah do it right. This can often have the effect of causing us to see how far we have strayed from a certain mitzvah.

Choose a mitvzah you want to reawaken yourself to. Then think of who is the person that is the best at doing this mitzvah. For example, lets say you are trying to work on not saying Loshon Hara. And there is one guy in the yeshiva who is the great at maneuvering conversations away from Loshon Hara. Arrange to spend a Shabbos with him. Watch how he works. Learn his tools. And most of all, be inspired by his amazing qualities.

Once a Rabbi was sitting in Shul and someone approached him and started to speak Loshon Hara to him. He turned to the person with a warm and loving voice and said, “I have so many negative qualities of my own. Why do I have to hear about anyone else’s?” (Heard from a Rabbi in Aish Hatorah)

Once a student watched a Rabbi who was visibly late for a very important appointment take the time to say the Birchas HaMazon word for word with deep concentration. After the blessing the Rabbi said, “Just because I am clumsy enough to be late, should my prayers suffer? The student was deeply moved.

So find the experts in various mitzvahs and watch them do it right. Use this as a tool to inspire yourself to grow to where you should be.


One way to restore your sensitivities is to examine the foundations of your life. Take some time off between seder hours. Ask yourself the most basic questions:

What am I living for?
What am I doing and why am I doing it?
How much do I know that there is a G-d?
Do I really believe that Torah is true?
Do I really understand the power of Torah?
Why am I not as serious asI used to be? etc.

Many times during the year we work so hard that we lose sight of our priorities. We need to go back and ask ourselves why are we doing what we are doing. Many people have felt that one of the most powerful ways to return to that lost part of themselves is to examine their foundations. This sets apart those who fall into traps and those who don’t.

Don’t be scared to ask those questions that have been piling up inside you over the past twelve months or so. There is nothing wrong with working out issues. Find out where the holes are in your foundations and you will feel much better after you have filled them in. This is the time of the year to do such a cheshbon. This is the time to rededicate to get back to the basics of life and its purpose


The reason we lose touch with ourselves and allow ourselves to sin is because we don’t take time every day to reconnect with our deepest desires and essence. Therefore, the solution to the problem is the obvious: We have to spend time alone everyday and make it a habit to keep in touch with what we want and what we are doing here on earth. This will never allow us to drift very far from good.

The foundations of piety and the root of perfection in the service of G-d lies in a man’s coming to see clearly and recognizing as a truth the nature of his duty in the world and the end towards which he should direct his vision and aspiration in all of his labors all the days of his life. (The Mesillas Yesharim, Perek 1)


Hopefully, the previous ideas will serve to inspire us to find the deepest parts of ourselves that are lost and return them to where they should be during these very important Ten Days of Teshuva.

5.01 The Ten Days of Teshuvah: Understanding the Fast of Gedalia



One of the most difficult aspects to understand about the Ten Days of Teshuva is the Fast of Gedalia (Tsom Gedalia). Right in the middle of working very hard on ourselves and growing and focusing on the issues of Tishrei, the Fast of Gedalia is suddenly thrown in. And we all have asked ourselves, what is this doing here now, in Tishrei when we are working on the issues of the High Holy Days? What is the connection between the destruction of the Beis HaMikdash and the Ten Days of Teshuva? The purpose of this sheet is to answer these perplexing questions and focus us to the issues that we should be concentrating during this very important fast day.


After the destruction of the First Temple and the exile of the majority of the Jewish People to Babylon, the wrath of the conqueror, Nebuchadnezzar, abated. He displayed a gentler attitude to the Jews and allowed some of them to remain in the Land of Israel. He even appointed a Jewish governor as their leader. His name was Gedalia, the son of Achikam. When this became known, Jews who had escaped from the horrors of the war into neighboring countries gradually returned to their towns and homesteads in Yehuda.

Gedalia understood the role that the Jewish People needed to play at this point in history in their relationship to the nations of the world. He understood that they needed to be obedient to the nations where G-d had delivered them. He understood that G-d inclines the hearts of kings to any direction that He wants and the Jewish People therefore had nothing to fear if they did what was right.

But ‘the remnant of Israel’ that stayed behind could not yield to G-d’s plans. Yishmael, the son of Netaniah, spurred on by jealousy and foreign influence, arose .and ignored the will of the King of Babylon. He treacherously killed Gedalia and most of the Jews and Babylonians that were around him. The day that this occurred was the third day of Tishrei, fifty-two days after the appointment of Gedalia, shortly after the Al-mighty had started bringing some rest from their suffering to the remnant of Yehuda.

In the aftermath of Gedalia’s murder, the remaining Jews’ spirits had sunk to their lowest level as they dreaded the reprisal of the king of Babylon. They planned to descend to Egypt to save themselves. But Egypt was the most defiled and corrupt of all the nations, and the Jews dreaded going there. So they turned to the Prophet Yermiahu, who was secluded in mourning, to ask for advice. For forty years they had not listened to the Prophet’s warnings, and now they stood before him shame-faced like a thief who was caught. ‘We will now listen to all that G-d will tell us,” they promised.

Yermiahu now tried to communicate with the Al-mighty but a partition of iron seemed to separate him from Hashem. G-d did riot seem to be responding to the plea of the Jewish People who now wanted to do teshuva. They turned to Him during the Ten Days of Teshuva, but they soon realized that Hashem was still angry with them.

Finally, on Yom Kippur, the Jewish People were forgiven. After many days of waiting, Yermiahu called in the leaders and told them that everything would be okay. In the near future, Hashem would make Babylonia act mercifully towards the Jewish People and He would return them and all their exiled brothers to their own soil. But if they decided to go to Egypt, the sword from which they were running would kill them there.

The Prophet’s words did not penetrate their ears and hearts and they refused to believe. They just could not believe that G-d would allow them to live in the Land after everything that had occurred. The generals gathered the whole remnant of the Jewish People and went down to Egypt. Thus they caused the the banishment from the Land to become complete and final.

Just a few years later, Babylon conquered Egypt and the exiles from Yehuda were completely wiped out by the sword. They fell and died by the thousands and tens of thousands. Not a survivor was left out of the whole remnant of the exiles with the exception of Yermiahu (who was kidnapped by the generals) and some of his disciples. Yermiahu’s prophecy had become painfully true.

The murder of Gedalia ben Achikam extinguished the last spark of hope for a renewal of Jewish life in the Holy Land. Now the destruction had become complete. Within seven years, the Land turned into a barren desert. For fifty-two years all living creatures shunned it.

The day Gedalia was killed has been likened to the day when the Temple was destroyed because it caused the end of Jewish settlement in Eretz Yisroel for many years. The prophets declared that the anniversary of the tragedy should be a day of fasting. Thus, this day became a memorial to the murder of the righteous governor and the end of a Jewish precense in Yehuda. (Based on Toldas Am Olam, Horeb, and The Art-scroll History Series)


1. During the Ten Days of Teshuva we must realize that no matter how much we have transgressed. Hashem accepts our teshuva.

The Jewish People had sunk to one of the lowest levels ever in their history. Their Temple was destroyed, the majority of the Jewish People were exiled, and things looked hopeless. Finally, G-d decided to grant them mercy and change their desperate situation. By having Gedalia, a righteous man appointed, it looked as if the whole situation would radically improve. But things sunk even lower. Gedalia was murdered by a Jew and all hope was wiped out. At this point when the Jewish people were at their lowest level, they decided to do teshuva. This was during the Ten Days of Teshuva. Even at the height of His anger, Hashem relented and on Yom Kippur granted them forgiveness.

The fact that this story is memorialized during the Ten Days of Teshuva is no accident. It is to teach us the message of these days: Return no matter how far you are away and Hashem will forgive you.

2. There is an intimate connection between the Ten Days of Teshuva and the destruction of the Beis HaMikdash

The story of Gedalia is one of the saddest of the whole epoch of the destruction of the First Temple. It is so painful to hear about the opportunities to return that the Jewish People lost again and again. When we hear that a Jew murdered so many people, we are stunned and shocked.

The purpose of this day of remembrance is to get us to mourn the destruction of the Temple and the low level we descended to. By hearing this story, this will hopefully bring us to do teshuva on all our sins and bring back the Presence of G-d which we so desperately need.

How can I narrate the disaster when my sighing is so heavy. My soul is weary. My congregations are grieving. Our few remnants who have escaped the flames, even they could not stand firm and were scattered in wrath. How long still will You hide Your countenance from us? Hear our cry and loosen our bound ones. (Selichos of Tsom Gedalia)

During the Ten Days of Teshuva, when the opportunities to return to Hashem are the highest, we should mourn how far away from the Al-mighty we are, and this realization should bring us to teshuva.

3.Doing teshuva means submitting to G-d’s will at all times not iust when it agrees with what you want

Doing teshuva does not mean that you will listen to G-d only when you want.

The Jews who remained alive (after Gedalia’s murder), although not of such a wicked nature, still shared a deep-rooted tendency not to submit to G-d’s guidance. Although they were robbed of all outer independence, they still wanted to establish their affairs upon a basis of human independence and not G-dly dependence.

This became manifest again in the opposition to G-d’s command to wait for the clemency of Nebuchadnezzar. Their downfall was the result of their folly which would recognize as G-d’s will only that which coincided with their own. (Based on Horeb, R. Samson Raphael Hirsch, P. 144.)

This is another message for the Ten Days of Teshuva. Return to G-d in a real way in which you truly submit to His will no matter what. The leaders who went to Yermiahu to ask what to do only went because they were subconsciously sure that G-d would answer the way that they wanted Him to answer. When G-d didn’t answer the way they wanted Him to, they rebelled. It is very important during the Ten Days of Teshuva to ask yourself the question, am I submitting to G-d’s will only in the areas that I want or am I submitting even in areas that are not so comfortable for me?

4.During the Ten Days of Teshuva is the time to realize that not listening to G-d always leads to negative results

The leaders thought that it was impossible to stay in the Land and survive. Yermiahu told them otherwise. The outcome was that they ignored his advice and not one of them remained alive in the end.

This should be a lesson to us during the Ten Days of Teshuva. Even if all the evidence points in the opposite direction to that which the Torah says, listening to G-d in the end will lead to ultimate reward.

5.During the Ten Days of Teshuva is precisely the time to realize how important it is to be righteous

Many times during the Ten Days of Teshuva we might get discouraged by the difficulties involved in becoming righteous. And we wonder what is the whole teshuva process all worth. The story of the downfall of Gedalia is brought to clear away this confusion.

The Fast of Gedalia is enumerated together with the fast days for the destruction of the Sanctuary “to teach that the death of the righteous is as weighty as the burning of G-d’s house’ (Rosh HaShanah 18b). Years of great effort are needed to build a Sanctuary, and its benefits to the world are immense; but even more effort must be expended to develop a truly righteous man, and his death is an even greater loss than the burning of the Sanctuary. (Torah Nation, Avigdor Miller, p.13)

This information is brought to teach us how valuable it is to try our hardest to do teshuva during this very important time period.


The purpose of this sheet was to help us understand the connection between Tsom Gedalia and The Ten Days of Teshuva. We hope that these insights will help us realize the tremendous opportunity that is offered on this day and let us rise to seize that opportunity.

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