A Comprehensive Program to Maximize The High Holy Days

Category: Week Four

4.05 Week 4 – Understanding Teshuva and Selichos; The Power of Rosh HaShanah



It was taught In the name of R. Eliezer: The world was created on the twenty-fifth of Elul. The view of Rav agrees with the teaching of R. Eliezer. For we have learned In the Shofar Blessing composed by Rav: ‘This day, on which was the beginning of Your work, Is a memorial of the first day, for it Is a statute for Israel, a decree of the G-d of Jacob. On this day sentence Is pronounced upon countries. . . which of them is destined to the sword and which to peace. which to famine and which to plenty. Each separate creature Is remembered then, and recorded for life or for death. (Vayikra Raba 29.1)


Many of us approach Rosh HaShanah with subconscious negativity, “Oh no, now I am approaching Rosh HaShanah. Now I am getting judged by the King. If I don’t serve Him, I will be punished.” Because of our Western, Non-Jewish orientation, the issues connected with Rosh HaShanah often put into our minds a lot of negative associations. But if we examine these concepts from a Torah Perspective, we see that Judaism’s concepts are not negative, but beautiful and insightful.

In order to understand what Rosh HaShanah is all about, we have to ask some basic questions. The first question to ask is why did G-d create the world? Since we know that Rosh HaShanah symbolizes the creation of the world and more specifically, the creation of man, this is an important question to ask on this day.

The answer is, of course, that G-d created us in order that He could give us pleasure.

Our Sages, of blessed memory, have taught us that man was created for the sole purpose of rejoicing In G-d and deriving pleasure from the splendor of His Presence; for this Is true joy and the greatest pleasure that can be found. (The Mesillas Yesharim, Perek Aleph)

The purpose of all that was created was therefore to bring Into existence a creature who could derive pleasure from G-d’s own good, in a way that would be possible for It. (Derech HaShem 1.2.1)

G-d created the world in order to give to us. G-d wants us to have every good in the world. But there is a catch. The greatest form of creation is to make someone independent. Independence implies choice. So G-d created us with freewill, the ability to choose reality or deny it. If we choose good, then we merit the pleasure we receive. That is the greatest good possible to give. (For further information about this complex subject please read Derech HaShem, The Way of G-d, Chapter 2)

Therefore, G-d can’t directly give to us, unless we do the things that involve choosing properly. Now comes the dilemma: G-d created the world with the sole purpose to give but He cannot give unless we merit it.


The day of Rosh HaShanah is the birthday of mankind. On the sixth day of Creation, the first day of Tishrei, man was created. Every year the process repeats itself; G-d has to decide to recreate mankind. Every year, G-d allows us to earn our lives back. Therefore, every year we must re-earn the right to exist.

On the day of Rosh HaShanah, G-d wants to recreate the world, and he wants to create us anew. This is because He loves us. To do so, He needs us to choose reality. He needs us to choose life.

This is the meaning behind the concept, “The Day of Judgement: G-d judges us this day as to whether we are choosing reality. If we choose reality, G-d grants us a year of reality. If we choose to be asleep, G-d grants us a year of death; a year of being asleep to the meaning of life and truth. But the main point is not that G-d is doing this because He wants to punish us, but rather because He loves us. He wants us to succeed. But we must choose on our own.

Rosh HaShanah is the birthday of freewill. It is the birthday of ultimate choice. Do you decide to be recreated as a soul or do you decide to be as if you are dead, roaming the world asleep all year long?

So when the day of Rosh HaShanah comes, it is as if G-d is saying, “Hello, I created the world and I want to give you every pleasure possible. Please do the things that allow Me to give to you.’ All G-d wants to do is to give, and it pains Him not being able to give to us in the way that He wants to.


The day of Rosh HaShanah is the day of realizing who G-d is. G-d is the King. G-d is all powerful. G-d is the Creator. G-d is the Ultimate. Internalizing these concepts is the greatest form of choosing, because it is the ultimate form of understanding truth.

But for many of us, when we hear these concepts we have a bad taste in our mouth. We think of the twentieth century concept of a king. We think of a king as a despot, a greedy and power-hungry individual who wants to subjugate the masses for his devious aims.

The Jewish concept of a king is that he is a servant of the people (See Rambam, Hilchos Melachim 2.6). He is someone who loves and cares about his people. His only concern is that the people live in happiness and harmony. The only reason he make decrees and laws is for the good of the people, not for himself.

This is the purpose of Rosh HaShanah. The purpose of Rosh HaShanah is to crown G-d King. We choose Him as the ruler and director of our lives. We are not doing this for Him but rather for us; now He can give to us and He can shower us with His goodness and love so that the purpose of Creation will be fulfilled.


These concepts put Rosh HaShanah in an entirely new light. Realize we are subjecting ourselves to a loving and beneficent King who make decrees for the benefit of His people.

The main reason to choose G-d on Rosh HaShanah is not for Him. It is for us. It is so we can benefit from the pleasure of His goodness. It is so we can experience the great things that His world has to offer. We must choose G-d so we can allow Him to give to us. Without Him, our ability to succeed in life is impossible.

Rosh HaShanah is the day where G-d desires to give. G-d is begging us to shape up so He can give us life. We have to make ourselves worthy of receiving Hashem’s abundant blessings.


The object of Rosh HaShana is not to pray for a good year. Its sole purpose is to make G-d ruler over us. We have to ask G-d to rule over the world. In order for Hashem to rule over the world, however He must have subjects and that is what the day of Rosh HaShanah is all about.

This explains why on Rosh HaShanah, there are no confessions in the machzor, for unlike Yom Kippur, teshuva on our daily sins is not the purpose of the day. The purpose of the day is to set our values straight and to return to the reality of G-d as King.This davening emphasizes this again and again.

This is one of the many meanings of the Shofar. We are blowing the shofar to crown G-d as the King. We are blowing to proclaim to the world: HaShem is the ruler of the world. May He reign forever. And we hereby dedicate to Him totally.


The mussar seforim emphasize over and over again the opportunities for greatness that are available on Rosh HaShanah (see Miktav Me’Eliahu, Chelek Beis, p. 68). Because we are recreated on this day we have the ability to rise to heights that are not available the rest of the year. We have the ability to recreate ourselves to a much higher level than we ever dreamed possible. To a great extent, whatever our level is on Rosh HaShanah that will be our level for the whole year.


On Rosh HaShanah, choose greatness. Choose the Al-mighty totally without any reservations. This is the day to awaken to reality. If you choose it, you have the ability to reach unlimited heights. So please take the opportunity to succeed. Your whole year depends on it.

4.03 Week 4-Understanding Teshuva and Selichos; Pathways to Cheshbon – Part 1



One of the key elements of your commitment to the teshuva process is to have a plan. Without one it is hard to show G-d that you are seriously committed to change in the future.

The first step in making a plan is to figure out your goals in life. What do you want and which direction do you want to take? Once a person determines his goals, he then begins to implement and monitor them. This sheet contains suggestions for determining yearly and lifetime goals. Tomorrow’s sheet deals with how to monitor your goals.


The Baalei Mussar (the masters of self perfection) speak about the absolute necessity of self-reflection and awareness on where you are and where you need to go:

A man must constantly — at all times, and particularly during a regularly appointed time of solitude — reflect upon the true path (according to the ordinance of the Torah) that a man must walk upon. After engaging in such reflection, he will come to consider whether or not his deeds travel along this path. For in doing so it will certainly be easy for him to cleanse himself of all evil and to correct all of his ways. (Mesillas Yesharim, Perek Gimmel)


This sheet is not suggesting that you try out all the exercises here. Rather, it is written as a list of options so you can have a choice. Try one and see if the tool is for you. If not, try another one. More than that might be too much.


This pathway suggests that we write down the personal resume that we would write one year from today — if all our dreams came true. Many of us have a work-oriented resume summarizing our past work history. We could do the same for our past personal history. This tool suggests writing a future resume now as if we were summarizing the next year. It will then tell us what we want to happen over that period.

There are three rules governing what goes into your “future” resume:

1. It has to be something you want to happen.
2. It has to be possible (even if you don’t plan for it to happen, or even if it would require great energy output on your part).
3. You have to be as specific about it as possible.

What do you do after you finish your resume?

Look at all the ideas written on the paper. Ask yourself, ‘Why can’t I make this a reality?’ Brainstorm different ideas to overcome potential obstacles from getting you where you need to go.

What is the purpose of the “future” resume?

Many people have unconscious goals and wishes that are buried deep in their personality. They think they never can achieve them. If they make them conscious, they may well see that they can achieve goals that they never thought possible.

For example, you may have a strong subconscious wish to finish a certain mesechta. But you avoid thinking about it because you don’t believe it is possible. By doing this exercise, this desire might come to the surface. Then you might take action for achieving it.

Many times you have a goal that you wouldn’t even consider because your Yetzer Hara has you convinced that it is just not possible. Doing this exercise might get you to realize aspirations that you might not normally concentrate on.

Note: This exercise can be done for a longer period than one year. Pretend you are 120 years old, sitting in a rocking chair looking back on your life. What would you want written about your life that went before. This provides incredible insights into what you want out of life.


What are your lifetime goals?
How would you like to spend the next three years?
If you knew now you would be struck by lightning six months from today, how would you live until then?

Get several pieces of paper, a pencil or pen, and a watch or clock with a second hand. Set aside about fifteen minutes. On the top of a sheet of paper write the question: What are my lifetime goals?

Now take two minutes to list answers. Of necessity, you will have to stay very general and abstract, but you should still include all the areas you can think of. Make your list as all-inclusive as you can. During this listing stage you are not committed to any of the goals that write down, so record whatever comes into your head.

After the first two minutes are up, give yourself an additional two minutes to make the changes necessary for you to feel satisfied with your statement of goals at this early stage.

The Second Lifetime Question — When you list lifetime goals quickly and without much reflection, you probably include a number of generalities such as happiness,’ success, achievement,’ and the like. You can pinpoint your goals better by now asking a second question: How would I like to spend the next three years? Again list your answers as quickly as possible for two minutes. Then take another two minutes to include whatever you may have missed the first time around on this question.

The Third Lifetime Question Now, for a different perspective, write down this third question: If I knew now I would be struck dead by lightening six months from today, how would I live until then?

The purpose of this question is to find out whether there are things that are important to you that you’re not doing now or which deserve more of your attention in the next six months. You might continue to live as you are now or you may want to add several things that are missing. Write your answers as quickly as possible for two minutes, then go back and refine them for an additional two minutes. (Don’t get lost in thinking about this question — just write.)

Working Further On All Three Questions Now spend an additional two minutes minimum reviewing and improving your goals statement on all three questions. You may spend longer if you wish.

Take your list in hand and spend one minute selecting the top three goals in each question.

At this point, you should have nine goals culled from the three lists. To pick out the three most important long-term goals of the nine, write on a fresh piece of paper, “My three most important long-t,erms goals are …” Then write them in priority order. You have now finished a preliminary goals statement.

You might want to try this exercise a few times until you are clear with exactly what you want out of life


Write out a list of all the major areas of your life. That list might include learning, serving G-d, interpersonal relations, financial concerns, community responsibilities, etc. Try to be as comprehensive as you can. Write on the top of a piece or paper the following question: I would have more satisfaction one year from now in each area if…

Then start brainstorming ideas in order to fill in the blank. After fifteen minutes of doing this, you will have a list of directions you might want to change in.

Now come up with specific, practical solutions to allow you to have more satisfaction in your problem area. Implement them in a weekly program and you will start seeing tangible change in how you feel about your life.


King Solomon said, ‘If you search for it like silver, and hunt for it like a treasure, then you will understand the fear of G-d.” What King Solomon is trying to tell us is to treat our spiritual growth as seriously as we would search for treasure. Another way of looking at it is, we should pursue growth the same way we pursue money in our lives.

This pathway is for individuals with a business background or with a business type orientation. It suggests that we should make a long term plan for our lives in the same way a company would make one. Every company has a plan with directions, dates and deadlines for each step in their future. We should have one as well.

So sit down and make a plan for the future. Ask yourself how you would make such a plan if you owned a business. By doing this, you can come to many different insights into how you should take your life more seriously.


In order to begin work on the Teshuva process, one needs to know what he wants out of life and where he wants to go. Once he has that clear it will allow him to develop a plan for Teshuva that will lead to maximum growth and direction.

This sheet is dedicated to getting us to delve inside ourselves and figure out what we really want and are looking for in our lives. Out of this we can develop a plan for teshuva that will motivate, and excite us in a powerful way.

So now pick a pathway and try it. You will find that it will open you up and allow you to think of the directions you need to pursue in the future.

4.02 Week 4 – The Power of Cheshbon What Do I Do Teshuva On?



We are now beginning the final week of the month of Elul. According to the Rosh HaYeshiva’s plan (see sheet #1), now is the time to intensify the process of Cheshbon (spiritual accounting) and come up with a plan for change. The first week we woke ourselves up to the month of Elul. The second week we worked on our relationship to G-d. The third we worked on Teshuva and Selichos. Now we are ready to get down to the serious business of Cheshbon which includes evaluating and planning for the future.


It is important to keep in mind that this is the last week of the year. This has very deep spiritual significance:

The Sages have written that just as we say “hakol holeich achar hachitum,” (everything is determined by the end), so, too, we can make amends for all the days of the year by rectifying the days of the last week of the year. How one conducts himself on the last Sunday of the year will be considered as how he conducted himself on all Sundays throughout the year. Similarly for Monday, Tuesday, etc. Since Shabbos is the holiest day, it is especially appropriate to strive to conduct oneself in a more perfect manner of Shabbos observance in an atmosphere of Shabbos sanctity. This will credit all the Shabboses of the year as having been conducted in like fashion. (The Shelah HaKodesh quoted in The New Rosh HaShanah Anthology).

When someone does teshuva at the end of a major time period, the whole period prior to the teshuva becomes sanctified. The most well known example of this is someone who does teshuva on his death bed. This important piece of information should spur us on to be particularly careful this last week of the year.


When one begins to look at the task of teshuva, it can be overwhelming. We have done so many misdeeds 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 to our transgressions and attack those root problems, eventually, most of our transgressions would fall away. So if one says to G-d in truth, “G-d, here is my plan that I think will allow me to wipe out my transgressions in the shortest amount of time possible,” then G-G-d will accept him back totally

The goal of the teshuva process at this time of the year is to figure out the root of what is holding a person back and attack it in the most powerful way.(Rav Yitzchak Berkowitz in his tapes on Elul and the High Holy Days)


Imagine a new child taking his first steps in front of his proud parents. He gets on his feet and takes a few steps and falls flat on his face. The parents clap with joy and happiness. But if you analyze the situation, shouldn’t the parents be upset? After all, the child fell down. The answer is obvious. A parent doesn’t judge a child based on whether or not he fell, but rather on whether he took the steps necessary to go in the right direction.

So, too, with the Al-mighty. If we return to the Al-mighty with all our heart and all our soul, but we are too weak to commit to instant change, the Al-mighty won’t judge us for that. The thing that concerns Him is if we are moving in the right direction with the proper effort that is demanded of us.

So G-d looks at us and sees: Is he trying? Is he committed to change? Since the Almighty can see through time, He can look to see if you really meant it when you said that you would stop doing the transgression in the future.

The goal of the teshuva process is to make a plan that will liberate us from the things that hold us back. This requires the ability to evaluate where we are at and where we need to go. As we have mentioned the word for this in hebrew is called Cheshbon which means an accounting.”


It is obvious that G-d does not command you to have every aspect worked out. You may not have the ability or the understanding to do such a thing. What you can do is to plan the directions that you think will best move you closer to G-d.

For example, take the five best ideas that you think will lead you to successfully and implement them. This is a worthwhile effort in Hashem’s eyes. An individual doesn’t need to know all the answers to everything right now. The key is the commitment to change.

A good analogy is the American Space Program of the 1950’s. The Americans had never gone to the moon before. They at that time didn’t even know how to send a man into outer space. What they had was the resolve to take the next step based on all the available information at the time. And with that resolve they put a man on the moon.

So, too, with your personality. Make a general plan of how you think you will succeed. Resolve to commit to success. Take your next step at the soonest possible time and G-d will consider that Teshuva.


“There is nothing that stands in the way of free will,” (Alel Shor, perek 25) …

“In the way that a man wants to go he will be led,” (Makos, lOB) …

The secret of free will is wanting (chefetz) which is the highest thing in all creation. . . It is incumbent upon us to know this powerful truth: What a man really wants, this is what he will achieve in life, and the opposite is true: What a man achieves in his life, this is a revelation of what was his will in the beginning. (AIei Shor, perek 25)

All over the Torah there is statement after statement telling us one thing: Strengthen your will in a certain area and you will achieve success in that area. There is nothing that can stand in the way of someone with a true desire.

This is the secret of teshuva for the High Holy Days: Commit to a full return to G-d from the bottom of your heart and that will eventually wipe out all your sins. Dedicate yourself to a plan to wipe out transgression and you will have done complete teshuva during this most important time period.

4.01 Week 4 – Understanding Teshuva and Selichos; Understanding Selichos



Last night many of us participated in the Selichos Service. The Selichos Service consists of special prayers for forgiveness that our Sages instructed us to say the days before Rosh HaShanah and during the Ten Days of Teshuva. The goal of these prayers is to motivate us to complete our Elul preparations and to warm us up for the intensive activity of Rosh HaShanah and Yom Kippur.

King David knew that in the future the Beis HaMikdash would be destroyed and the use of sacrifices would cease because of the sins of the Jewish Peopie. King David was troubled because he didn’t know how the Jews would get atonement for their sins. The Holy One said to King David, “At the time that troubles come to the Jewish People because of their sins, let them say before me the order of the Selichos Prayers (the 13 Attributes) and I will answer them. (Tanna D’be Eliahu Zuta, Perek 23)


The Ashkenazi Community follows the custom of beginning Selichos at least four days before Rosh HaShanah. The reason for this is the following:

The Sages point out that in reference to bringing sacrifices, on all the other festivals the Torah writes merely v’hikravtem, and you shall bring an offering (BaMidbar 28.19; 27; 29.8;13). However, in the case of the sacrificial offerings of Rosh HaShanah the wording Is changed to read va’asisem, and you shall “make an offering” (BaMidbar 28.2). This change alludes to the fact that before Rosh HaShanah a Jew must prepare himself as an offering to G-d, creating himself a new person.

A sacrifice has to be free of all blemishes. The Torah requires that all animals used for sacrifices must undergo a four-day period of inspection and examination to ensure that they are free of any blemish, thus ensuring their fitness for sacrifice upon the altar. Similarly, four days before Rosh HaShanah, a Jew must inspect and examine himself to see that he frees himself from any spiritual imperfection which would invalidate his rededication to the service of G-d. (The New Rosh HaShanah Anthology, p. 26)

Four days is the absolute minimum required to inspect yourself of any imperfection. So, therefore, the Selichos process is giving us a powerful message: get to work and eliminate those remaining things holding you back from Rosh HaShanah perfection.


The custom is to always begin the Selichos Prayers on a Motsei Shabbos. If Rosh HaShanah falls on a Thursday, Friday or Shabbos, then it begins on the previous Motsei Shabbos. If, it falls on a Sunday or a Wednesday, the custom is to begin an entire week earlier.

Why do we always begin on Motsei Shabbos?

The Jew is filled with the spirit of Shabbos, the day on which he rests from the physical and mundane weekly matters. He spends the day in spirituality, Torah study, and reflection about G-d. Since this spirit of the sanctity of Shabbos flows over immediately to the weekdays, and Shabbos is a day of learning and pleasure, it was felt that in this mood one would be more adequately prepared for entering into the penitential frame of mind. Hence, Selichos are to begin on the night or early part of the day immediately following Shabbos. (The Leket Yosher (O.C. p. 118) quoted in The New Rosh HaShanah Anthology, p. 27)

The fact that Selichos falls on Motsei Shabbos underlines their importance. Four days before Rosh HaShanah would be enough. But in order to guarantee their success, the Rabbis sometimes move it up to as much as nine days early so that we can say them on a Motsei Shabbos. The Selichos Prayers are so important that no obstacle must get in its way. That is why it begins each time on a Motsei Shabbos.


Now begins a whole new level in the teshuva process. It is the fourth week of Elul, and you have worked on yourself during the first three weeks of the month. You have tried to wake yourself up to your responsibilities, you have worked on your relationship to G-d, and you have begun to investigate the teshuva process. Now is the time to get much more serious.

We come before G-d and we realize where we are holding. We realize how far we are from where we should be and we stand in shame before G-d:

To You, 0 G-d belongs righteousness, but to us shame of face. How can we complain? What can we say? What can we speak? Or how can we justify ourselves? Let us search and examine our ways and return to You for Your right hand is outstretched to those returning to You. Not with virtue, nor with good deeds, do we appear before You, but like the poor and the needy we knock at Your gates. We knock at Your gates, 0 merciful and gracious One. Please do not turn us away empty from Your presence. From Your presence, our King, turn us not away empty, for You hear our prayers. (from the Selichos prayers).

The Selichos Prayers are a warmup for the whole teshuva process that is getting more and more intense. We must ask ourselves: Are we humble before G-d? Do we realize where we really are holding? Do we really understand what we have really done during the past year? And don’t we really have to ask Him to truly forgive us? This is the purpose of the whole Selichos process.

The word ‘Selicha” means forgiveness. What frame of mind should one be in who asks forgiveness? What are the emotions involved? How does one proceed? The Rabbis have taken the answers to all these questions and formulated a set of prayers that are designed to bring us to a state of humility conducive to asking forgiveness and doing teshuva.

A ten year old boy stole ten shekels from his father to buy a toy that he wanted from the store. The toy costs twenty shekels so he figured he would go to his father to ask for the other ten shekels. He went to his father to ask for the other ten shekels. His father looked him in the eye and gave him a warm and loving smile and said, ‘You have been such a good boy, here is twenty shekels so you can buy the whole toy.” The little boy immediately burst into tears. (Story heard from a friend).

This story is an indication of how we should feel during Selichos if we truly understood how many things we have done to our Father-In-Heaven.


The Selichos prayers are approximately 30-40 minutes long. We will be saying them every day except for Shabbos until Yom Kippur (for a little more than two weeks). For someone experiencing his first or second High Holy Days cycle, the experience might be very overwhelming. Therefore, it is important to find an older student who will sit down with you and explain to you the basic structure of the prayers. Then spend five to ten minutes a day trying to understand the meaning of a section of the service. During the service try to have cavannah (mindful intention) specifically on that section.Those who have done no preparatory study of the Selichos Service usually find it to be quite painful and difficult.


The Selichos prayers have already begun. They are a tremendous opportunity for actualizing many of the feelings we want to express but don’t know how. For those who prepared and want to use this tremendous tool, the opportunity lies before you. Use this year to learn how to utilize the Selichos service, and you will feel the powerful difference it makes in your teshuva process.


There is another type of person who has a lot of pain when saying Selichos. They are the people who have not worked during the whole month of Elul. They approach Selichos with a remark such as ‘Now I better get to work.’ And now when it comes time to ask forgiveness they are not emotionally prepared. It is very hard to wrench oneself into the High Holy Day atmosphere immediately without preparation.

Even for this type of person, there is a solution. They should do teshuva on the fact that they haven’t prepared themselves during Elul. They should make a commitment from now on, for all the Elul months they will be having in the future to utilize them properly. Then G-d will surely grant them success this year in their Avodah.

Meanwhile, start getting to work. Try to come up with an approach how you can integrate the main points of the upcoming season into your life. Ask advice of a Rebbe or an older student as to what you can do in order to be effective. It is not too late. Do your best and you will see that your efforts reap rewards.

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