Rosh Hashana 5778


The days between Rosh Hashana and Yom Kippur are referred to as “Aseres Y’mei Teshuva”, the Ten Days of Repentance. Their entire focus is the Mitzvah of Teshuva. The Rambam dedicates a complete volume in his Mishna Torah to the subject, writing more material on this topic than he does for the Mitzvos of Shofar or the Arba Minim. Likewise, Rabbeinu Yonah authored Sha’arei Teshuva, an entire sefer devoted solely to the Mitzvah of Teshuva.
Clearly, the Mitzvah of Teshuva is not something that can be performed without adequate understanding and preparation. Teshuva requires involvement. It is no less a Mitzvah than eating matzo; the same painstaking preparations that go into making a Seder are expected to be expended in performance of the Mitzvah of Teshuva.
Yet the Mitzvah of Teshuva is very different from Pesach preparations. The preparations we make for Pesach and similar Mitzvos are physical in nature – “work” in the very literal sense of the word. Teshuva differs greatly from these other Mitzvos. Teshuva requires not body but soul, one’s thoughts and emotions. It is obvious that one cannot just go through the “motions” of Teshuva. Teshuva requires “Kavana”, intention, not as an addition but as an integral part of the Mitzvah itself.
One must internalize the components of Teshuva – to comprehend the Teshuva process, allowing it to penetrate his being. Yet here again Teshuva is a unique Mitzvah. Whereas regarding other Mitzvos the preparations are just preparations, the essence of Teshuva is coming closer to Hashem. Any step towards that goal becomes the goal itself; the journey towards Teshuva is the very destination. The more we contemplate Teshuva, the more we pursue the Ribbono Shel Olam.
Rabbeinu Yonah lists the steps of Teshuva. The first step is חרטה, Remorse. The second step is עזיבת החטא, Forsaking Sin (which is not the focus of this discussion). The third step recorded is יגון, Sorrow. Remorse and Sorrow are closely related. What sets them apart in the Teshuva process? Simply understood, חרטה means, “I feel bad,” andיגון means, “I feel worse.” What divides them into two distinct levels within Teshuva?
Rabbeinu Yonah himself seems to address the question. כי יתכן שיתחרט וירע בעיניו על חטאתו אשר חטא…כי גם הפסד דינר קשה בעיני בני אדם, אך אם אבד עשרו בענין רע נפשו עליו תאבל ונפשו מרה לו, loosely translated, “It is possible that one feels remorse for his sin but has not yet fulfilled his Teshuva obligation, for one will be bothered if he loses a small sum of money, but when he loses all his wealth, then he will feel bitter and a sense of mourning.” Rabbeinu Yonah is likening Remorse to losing a small sum and Sorrow to losing all one’s wealth, but the question remains. That seems to be only a difference of amounts, not something inherently different, sufficient to create separate steps in the Teshuva process.
Rabbeinu Yonah makes another point aboutיגון . He explains that יגון, Sorrow, emanates from the soul. Coming from the soul, it is more readily accepted by Hashem. He compares it to a king dealing with his subjects. The king will more likely forgive those closer to him than those more distant. So, too, when what is closer to Hashem cries out, the Ribbono Shel Olam has more compassion. That which is close to Hashem is the soul. יגון, Sorrow, is the cry of the soul. When the soul cries out to Hashem, it kindles His compassion.
But Rabbeinu Yonah does not explain why sorrow comes from soul. It does come from the soul and therefore arouses G-d’s empathy, but why does it come from the soul?
The process of remorse is the beginning of Teshuva. At the beginning of Teshuva, one makes an assessment of his decisions and concludes they were wrong. He faces his actions and he questions his foolishness of choice. He looks at himself in bewilderment. “How could I have been so foolish?” One begins the process of Teshuva by disconnecting himself from the choices of his past, thereby removing his connection with sin. That is the process of חרטה, disengagement from sin. One doesn’t squander his money. One who loses money acknowledges the paucity of his decision, deriding himself for poor judgment: “Bad choice. What was I thinking?”
All that is within Remorse. Sorrow does something very different. One who loses his entire wealth isn’t simply suffering from a bad decision; rather, he is a changed person, his whole life’s course having been altered. That brings Sorrow. The Sorrow of Teshuva enables the person to redirect his course. It is only after one understands the magnitude of sin, appreciates the ability of the sin to alter one’s life in a detrimental fashion, that one can begin to redirect himself back on course.
This can only come from the soul. Only the soul feels the anguish of sin, because it is only the soul that lives with purpose. Sorrow seeks to awaken one’s mission of purpose. Lamenting the squandering of purpose enables one to find the true purpose – service of Hashem. Asserts Rabbeinu Yonah, יגוןis the cry of the soul.
This becomes two distinct steps within the Teshuva process, referred to as חרטה and יגון. The Teshuva process begins with חרטה severing our connection withחטא . It continues withעזיבת החטא , ensuring that the separation remains. Then, withיגון , we discover purpose in life.

At the commencement of both Shabbos and Yom Tov, there is a Halachic obligation to sanctify the day. Although the two requirements are similar in nature, there is a fundamental difference between them. Whereas the Kiddush of Shabbos is a Biblical obligation, the Kiddush of Yom Tov is a Rabbinic injunction.
The difference is not only conceptual. There is a practical application as well. The Gemara (Rosh Hashana 28a) asks if one is required to have specific intent when fulfilling Mitzvos, or if it is sufficient to intend to do the act without intending to perform a Mitzvah. For example, when one eats matzo on the first night of Pesach, must he have specific intent to fulfill the obligation of “eating matzo on the first night,” or is knowing that one is eating matzo, regardless of his intent, sufficient to be considered as having fulfilled his obligation?
The general rule in Halacha is that regarding Biblical obligations, one is required to have specific intent, whereas regarding Rabbinic obligations one does not (M.B. 60:4).
The Magen Avraham (O.C. 271) issues a ruling regarding the Friday night Kiddush. If one has recited the Tefillos of Shabbos, he has fulfilled his Biblical obligation of Kiddush, in which case the actual recital of Kiddush over the wine becomes Rabbinic in nature and carries with it certain Rabbinic leniencies.
The Mishna Berura questions this ruling. Since the Kiddush of Shabbos is Biblical, it requires specific intent to fulfill the obligation. When one recites his Tefillos, he presumably does not have specific intent to perform the Mitzvah of Kiddush. If so, he has not fulfilled the Mitzvah, and all the stringencies of Biblical obligations should pertain to his Kiddush recital.
This addresses the Kiddush of Shabbos. Regarding the Kiddush of Yom Tov, the Magen Avraham’s assertion would remain correct. (The Mishna Berura does raise other issues with the Magen Avraham’s position, which would also question the use of such a ruling for Yom Tov.)
The Chasam Sofer (O.C. 271) makes a fascinating point. Even though the Kiddush of Yom Tov is Rabbinic, the Kiddush of Yom Kippur is Biblical! (He bases his statement on a Rashi and Tosafos in Maseches Shavuos.) Yom Tov, he writes, includes a positive commandment of “Simcha,” festivity. Therefore, Yom Tov possesses a clear recognition of being a unique day. Shabbos, on the other hand, has no Biblical requirement for festivities, so there is no defining positive action to declare Shabbos special. The Mitzvah of Kiddush serves to fill that void. Similarly, Yom Kippur has no positive action to define its holiness, so there is a Biblical requirement to recite Kiddush on Yom Kippur.
Consequently, rules the Chasam Sofer, since the Kiddush of Yom Kippur is Biblical, and when one performs a Biblical commandment he is required to have specific intent, one reciting Tefillos on the night of Yom Kippur should have specific intention to fulfill the commandment of sanctifying the day.
This Halacha is particularly pertinent when Yom Kippur falls on a Shabbos. Even if one disagrees with the Chasam Sofer regarding Yom Kippur, on Shabbos the Mishna Berura’s position opposing the Magen Avraham applies.