Rav Hai Gaon teaches that the custom to blow shofar at the end of Yom Kippur is based on the Torah obligation to blow shofar on the Yom Kippur of the yovel (the jubilee year). The Kol Bo says it is meant to confound the Satan. The Meiri concurs with this second reason but the Shibolei Haleket, the Mordechai, and the Tur mention the first reason. Tosfot in Shabbat offers a third explanation. The shofar blowing proclaims that night has fallen and that one is now permitted to prepare the festive meal of motzai Yom Kippur. Many rishonim suggest other reasons, among them that it is a sign of the Divine Presence ascending to the heavens.

Why do we blow shofar every year if the shofar of yovel was only blown once in fifty years? In addition, if the shofar was only blown in Eretz Yisrael during yovel, how does it connect to motzai Yom Kippur when the shofar is blown everywhere? Rav Hai Gaon explains that there is a doubt when yovel falls out. Therefore, we blow shofar in every year. This still begs the fundamental question: What is the connection between yovel and Yom Kippur?

The Meshech Chochma discusses the sanctity of yovel and shemitta (the seventh year). While both relate to the land, shemitta is connected to Shabbat while yovel corresponds to Yom Tov. Shemitta and Shabbat both have inherent holiness, while yovel and Yom tov are dependent on the sanctification of the Jewish people. We say in Kiddush of Yom Tov, "Mekadesh Yisrael v'hazmanim." Likewise, Yovel is established through the proclamation of the Jewish court and its holiness is dependent on our actions.

Yovel signifies repentance and freedom. Property is returned to its original owner, slaves are set free, and liberty is proclaimed throughout the land. While shemitta focuses on the earth, yovel involves the individual. Rashi says the term yovel refers to the blowing of the shofar. Rav Kook explains that yovel is a kind of social and economic revolution necessary for the equilibrium of society. Similarly, the purification of Yom Kippur is the ability to transcend the shackles of the evil inclination. It proclaims freedom from the desires of the yetzer hara. On Yom Kippur, we become like angels divested of physicality. Likewise, yovel has an element of the world to come where the satan cannot rule. 'Hasatan' is the numerical value of 364, which signifies the 364 days of the year when the Satan has permission to meddle in our lives. One day in the year, Yom Kippur, we return to our source and are set free of his overpowering influence.

The shofar blast at the end of Yom Kippur heralds the realization of the ideals of yovel. We once again enter the lofty realm of alma d'teshuva (the world of repentance) and alma d'cherut (the world of freedom).

In the Torah, Yom Kippur is referred to in the plural form as Yom Hakippurim. Rav Soloveitchik explains that atonement is associated with sacrifices, which were a major part of the Yom Kippur service. The Rambam writes that since today there are no sacrifices, teshuva atones for all of our sins. Referring to Yom Kippur in the singular might lead us to think that we cannot attain atonement today because we don't have korbanot. Therefore, it is referred to as Yom Hakippurim

Every person approaches teshuva with his particular background. There's repenting from fear and repenting from love. A person can do teshuva while he is still young or when he reaches old age. Therefore we say, Yom Hakippurim to allude to the many different types of teshuva and the varied levels of atonement. Another reason for the plural form is that Yom Hakippurim also applies to atonement for the dead and the living. In fact, the practice to recite Yizkor was originally associated with Yom Kippur. The dead, whose judgment is ongoing, achieve atonement on Yom Kippur too.

In the Torah, vidui is discussed in the context of korbanot. It is not mentioned in relation to Yom Kippur. During the times of the beit hamikdash, the procedure a person underwent to purify himself literally transformed him into a new being. This is the essence of Yom Kippur. A Jew must become a different person to the point where he can say to Hashem, "The decree you placed upon me doesn't apply anymore." This encapsulates the concepts of teshuva and tahara (purification). The idea of mechila (forgiveness) has its roots in monetary law where a person can forgive a liability. Similarly, we ask Hashem to overlook our debt of sin. When a person purifies himself it's as though his sins are completely erased. In the Yom Kippur prayers, we say, "Ki bayom hazeh yichaper aleichem l'taher etchem." The essence of Yom Kippur is purification and the power of the day itself brings atonement, even without korbonot. According to one opinion the atonement comes even without teshuva. That is why there is such joy on Yom Kippur, and especially at its culmination.

Our sages tell us that when a person does teshuva out of love, "z'donot naasu lo k'zechuyot," his intentional sins becomes merits. How do we understand this?

We become a different being when we repent. The same energy and creativity that we invested in sin is now put into mitzvot

Selichot are prayers of forgiveness. The central motif is the recitation of the thirteen attributes, which appears numerous times throughout Neila. If we want to be the beneficiaries of Hashem's chesed we must live up to these attributes. We don't recite the full vidui during Neila. This is because we've already confessed our specific sins throughout the day. Yom Kippur is supposed to lead us to something beyond this, to a place where our focus turns to our central mission in life and our true goals.

Before Mincha on Yom Kippur, we read the maftir of Yonah. The commentators tell us that this section was chosen to remind us of the power of repentance. There are two aspects of mitzvot and aveirot. The first view is that they are meant to engender discipline and compliance. The commandments themselves aren't necessarily beneficial or damaging; it is only the results that are. The second view is that they are like a doctor's orders. Hashem tells us what is good or detrimental for us. The mitzvot have an inherent effect on us. In truth, both aspects are valid. We don't understand the intrinsic reasons for the mitzvot and aveirot, but if Hashem commanded or forbade something, it is for our good. The commandments affect us on an internal level. Mitzvot will strengthen our bond with Hashem, while aveirot will weaken it.

During the vidui (confession), we say, "Selach lanu, mechal lanu." Selicha refers to the intrinsic damage caused by sin. This is the doctor aspect. It is the facet that is connected to the reciprocal relationship between man and Hashem. Only Hashem can obliterate the internal damage of sin. Mechal is the external aspect of forgiveness. Hashem can forgive us as a king for the outer part of sin and as a father on the intrinsic level.

Repentance consists of three steps: regret, confession, and resolving not to sin again. The critical factor of repentance is that the person should not commit the sin again. Charata (regret)is intrinsic atonement. The verbal medium of vidui enhances both aspects. Confessing sensitizes a person to the reality of Hashem's presence and his responsibility for his actions. Confession makes an impression on the person, and intensifies and prolongs the effects of his teshuva. The Maharal says sin distances us from Hashem and vidui reconnects us to the divine aspect within ourselves. Focusing on charata helps us realize where we've gone wrong. Kabala al he'atid rectifies the rebellion aspect of sin.

Rav Lugasi notes that the first component of teshuva is taking responsibility for your actions. Then you can feel remorse for the choices you have taken and try to rectify it at the point of conflict. Teshuva also involves tuning into our inner voice and asking ourselves honestly what Hashem would want us to do. Our conscious makes demands on us based on our spiritual level. Once we begin to listen to this voice, it gets stronger.

The second challenge of charata is to admit our wrongdoings. This is a great level because it goes against our natural ego. Charata and vidui must be addressed on both a macro and micro level. We must look at our individual sins and at our lives in general and ask ourselves, "Is my life going to waste because of my misconceptions?" Hashem knows our innermost thoughts and can see how we feel about our sins. If we can express real charata, then Hashem will accept our repentance. Rav Tzadok writes that if a person makes a sincere commitment to change but is later overpowered by his evil inclination, he's still considered a tzaddik.

Kabala le'atid is taking one thing on a concrete level as a representation of our desire to improve. Setting up a restriction to stop us from reverting back to sin shows Hashem that we want to repent. Making small resolutions such as learning the laws of proper speech or studying a sefer on prayer are ways to arouse ourselves to change. On Yom Kippur we experience true joy. There's pure clarity as we come full circle in our relationship with Hashem. Hashem is like the groom and we are like the bride and we tell him, "We're ready to take the step forward." This can have far-reaching repercussions.

Another theme in the book of Yonah is Hashem's mercy on all of his creations. If Hashem showed compassion for a foreign nation, he certainly desires to be compassionate towards us. Yonah is read at mincha, a time of eit ratzon (favor). Yonah asked Hashem for truth and justice. And Hashem answered, "I run the world differently." Humans have physical limitations but Hashem is all merciful. On Yom Kippur, we ask Hashem to judge us mercifully just as He did Yonah and the people of Ninveh.

May Hashem grant us complete forgiveness. May He wipe our slates clean and may we merit to begin a new year filled with promise and accomplishments.

Question:   

What is the correct hashkafic approach to dealing with failure? For instance, when we commit a sin that we resolved not to do again, or when we destroy relationships that we resolved to build. How do we maintain our self-esteem in the face of feeling worthless inside?

Answer:

We all fail at some point in life. The evil inclination's strongest weapon is despair. Tehillim says, "A tzaddik falls seven times and rises."

There are seven attributes we share with Hashem. A person could fail at each one but it doesn't give him an excuse not to get up again. The difference between a tzaddik and a rasha is not that a tzaddik never fails, but that he rises up the seventh time. You must get up and try again.

If you resolved not to do something and then did it again, the method you used didn't work. Be creative. Devise a different plan of action. If that too fails, think of something else. Realize that Hashemwill not judge you by your successes, but rather by your efforts. Failing is completely normal. Many times we look at great people and think they were born righteous. In fact most tzaddikim started out small and suffered many setbacks before they finally attained their elevated spiritual level.