Teshuva: Refining Character
ותנא דעצם עצם האי בתשעה לחודש מאי עביד ליה מיבעי ליה לכדתני חייא בר רב מדיפתי דתני חייא בר רב מדיפתי ועניתם את נפשותיכם בתשעה וכי בתשעה מתענין והלא בעשור מתענין אלא לומר לך כל האוכל ושותה בתשיעי מעלה עליו הכתוב כאילו התענה תשיעי ועשירי
The Gemara asks: And the tanna who learns a verbal analogy from the words “that same day,” “that same day,” what does he do with the phrase: “On the ninth day of the month”? The Gemara answers: He requires it, in accordance with that which Ḥiyya bar Rav of Difti taught. As Ḥiyya bar Rav of Difti taught: It states: “And you shall afflict your souls on the ninth day of the month” (Leviticus 23:32). But does one afflict oneself on the ninth of Tishrei? Doesn’t one in fact afflict oneself on the tenth of Tishrei? Rather, the verse comes to tell you: Anyone who eats and drinks on the ninth of Tishrei and then fasts on the tenth, the verse ascribes him credit as though he fasted on both the ninth and the tenth. The verse alludes to this when it states that the fast is on the ninth.

(א) סדר ערב יום כפור ובו ב סעיפים:
מצוה לאכול בעיוה"כ ולהרבות בסעודה:

It is a mitzvah for one to eat on Erev Yom Kippur and to dine lavishly.

Gates of Repentance, R. Yonah Gerondi, 4

VIII. And now that we are without sacrifices, because of our transgressions and the transgressions of our fathers, if one sinned through the promptings of the heart, or if he transgressed a positive commandment, let him read the sections dealing with burnt-offerings in the beginning of the portions Vayikra and Tzav; for reading the section dealing with the sacrifice stands us in place of offering the sacrifice, whether the reading be in the Torah or in the oral tradition, as our Sages of blessed memory have said, "If one studies the section dealing with a burnt-offering, it is as if he sacrificed a burnt-offering; if he ·r studies the section dealing with a sin-offering, it is as if he sacrificed a sin-offering; and if he studies the section dealing with a guilt-offering, it is as if he sacrificed a guilt-offering" (Menachoth 110).

And if one has transgressed a negative commandment and repented, let him be troubled by his transgression and long in anticipation of the arrival of the Day of Atonement for the gain-ing of acceptance before the Blessed One, whose will is the life of spirit and body and the life of every creation, as it is said, "Life is in His will" (Psalms 30:6). In this regard our Sages of blessed memory said, "If one sets a repast for the eve of the Day of Atonement, it is as if he were commanded to fast upon the ninth and tenth days, and did so" (Rosh Hashanah 9a), for he thereby shows his joy at the arrival of the period of his atonement, and this serves as testimony to his worry over his guilt and his sorrow over his transgressions.

IX. Also, on the other festivals we set a repast for the joy of the mitzvah, for the reward for joy over mitzvoth is great and exalted, as it is said, .. And now have I seen with joy Thy people that are present here, offer willingly unto Thee" (I Chronicles 29:17), and, "...because thou didst not serve the Lord thy God with joyfulness and with gladness of heart' (Deuteronomy 28:47). Because the Day of Atonement is a fast-day, we are required to set a repast for the joy of the mitzvah on the eve of · the Day of Atonement.

X. And again [we are required to set a repast], to strengthen ourselves to multiply prayer and supplication on the Day of Atonement and to take counsel with ourselves concerning repentance and its essentials.

(א) הוֹאִיל וּרְשׁוּת כָּל אָדָם נְתוּנָה לוֹ כְּמוֹ שֶׁבֵּאַרְנוּ יִשְׁתַּדֵּל אָדָם לַעֲשׂוֹת תְּשׁוּבָה וּלְהִתְוַדּוֹת בְּפִיו מֵחֲטָאָיו וְלִנְעֹר כַּפָּיו מֵחֲטָאָיו כְּדֵי שֶׁיָּמוּת וְהוּא בַּעַל תְּשׁוּבָה וְיִזְכֶּה לְחַיֵּי הָעוֹלָם הַבָּא:

(ב) לְעוֹלָם יִרְאֶה אָדָם עַצְמוֹ כְּאִלּוּ הוּא נוֹטֶה לָמוּת וְשֶׁמָּא יָמוּת בִּשְׁעָתוֹ וְנִמְצָא עוֹמֵד בְּחֶטְאוֹ. לְפִיכָךְ יָשׁוּב מֵחֲטָאָיו מִיָּד וְלֹא יֵאָמֵר כְּשֶׁאַזְקִין אָשׁוּב שֶׁמָּא יָמוּת טֶרֶם שֶׁיַּזְקִין. הוּא שֶׁשְּׁלֹמֹה אָמַר בְּחָכְמָתוֹ (קהלת ט ח) "בְּכָל עֵת יִהְיוּ בְגָדֶיךָ לְבָנִים":

(ג) אַל תֹּאמַר שֶׁאֵין תְּשׁוּבָה אֶלָּא מַעֲבִירוֹת שֶׁיֵּשׁ בָּהֶן מַעֲשֶׂה כְּגוֹן זְנוּת וְגֵזֶל וּגְנֵבָה. אֶלָּא כְּשֵׁם שֶׁצָּרִיךְ אָדָם לָשׁוּב מֵאֵלּוּ כָּךְ הוּא צָרִיךְ לְחַפֵּשׂ בְּדֵעוֹת רָעוֹת שֶׁיֵּשׁ לוֹ וְלָשׁוּב מִן הַכַּעַס וּמִן הָאֵיבָה וּמִן הַקִּנְאָה וּמִן הַהִתּוּל וּמֵרְדִיפַת הַמָּמוֹן וְהַכָּבוֹד וּמֵרְדִיפַת הַמַּאֲכָלוֹת וְכַיּוֹצֵא בָּהֶן מִן הַכּל צָרִיךְ לַחֲזֹר בִּתְשׁוּבָה. וְאֵלּוּ הָעֲוֹנוֹת קָשִׁים מֵאוֹתָן שֶׁיֵּשׁ בָּהֶן מַעֲשֶׂה שֶׁבִּזְמַן שֶׁאָדָם נִשְׁקָע בְּאֵלּוּ קָשֶׁה הוּא לִפְרשׁ מֵהֶם. וְכֵן הוּא אוֹמֵר (ישעיה נה ז) "יַעֲזֹב רָשָׁע" וְגוֹ':

(1) Because every man was endowed with self-will, as we have elucidated, it is meet that man shall strive to repent, to confess his sins by word of his mouth, and to dust off his hands from his sins, as a preparation for death after repentance, so that he may acquire life in the World to Come.

(2) Ever should man look upon himself as if he is nigh to death, lest he die during the interval, as a consequence whereof he will be outstanding in his sin; he should, therefore not tarry but repent presently. He should not say: "In old age I will repent", perhaps he will die before old age overtakes him. To this Solomon in his wisdom pointed, saying: "Let thy garments always be white". (Ecc. 9.8).1Pirke Abot, 2.15; Shabbat, 153a. C.

(3) Do not say that no repentance is needed save on sins to which action is attached, for example: prostitution, robbery, or theft. For even as it is necessary for man to repent from such, so it is necessary for him to search his bad tendencies, to turn in repentance from anger, from hatred, from jealousy, from deceit, from pursuing after wealth, honor, feasting and such like these; yea, from all of these it is necessary for him to turn in repentance. Indeed these iniquities are more grievous and more difficult for a man to be separated from than those which require action, for on such the prophet Isaiah said: "Let the wicked forsake his way, and the man of iniquity his thoughts" (Is. 55.7).

(ז) הָרוֹאֶה חֲבֵרוֹ שֶׁחָטָא אוֹ שֶׁהָלַךְ בְּדֶרֶךְ לֹא טוֹבָה מִצְוָה לְהַחֲזִירוֹ לַמּוּטָב וּלְהוֹדִיעוֹ שֶׁהוּא חוֹטֵא עַל עַצְמוֹ בְּמַעֲשָׂיו הָרָעִים שֶׁנֶּאֱמַר (ויקרא יט יז) "הוֹכֵחַ תּוֹכִיחַ אֶת עֲמִיתֶךָ". הַמּוֹכִיחַ אֶת חֲבֵרוֹ. בֵּין בִּדְבָרִים שֶׁבֵּינוֹ לְבֵינוֹ. בֵּין בִּדְבָרִים שֶׁבֵּינוֹ לְבֵין הַמָּקוֹם. צָרִיךְ לְהוֹכִיחוֹ בֵּינוֹ לְבֵין עַצְמוֹ. וִידַבֵּר לוֹ בְּנַחַת וּבְלָשׁוֹן רַכָּה וְיוֹדִיעוֹ שֶׁאֵינוֹ אוֹמֵר לוֹ אֶלָּא לְטוֹבָתוֹ לַהֲבִיאוֹ לְחַיֵּי הָעוֹלָם הַבָּא. אִם קִבֵּל מִמֶּנּוּ מוּטָב וְאִם לָאו יוֹכִיחֶנּוּ פַּעַם שְׁנִיָּה וּשְׁלִישִׁית. וְכֵן תָּמִיד חַיָּב אָדָם לְהוֹכִיחוֹ עַד שֶׁיַּכֵּהוּ הַחוֹטֵא וְיֹאמַר לוֹ אֵינִי שׁוֹמֵעַ. וְכָל שֶׁאֶפְשָׁר בְּיָדוֹ לִמְחוֹת וְאֵינוֹ מוֹחֶה הוּא נִתְפָּשׂ בַּעֲוֹן אֵלּוּ כֵּיוָן שֶׁאֶפְשָׁר לוֹ לִמְחוֹת בָּהֶם:

(7) He who beholds his fellow stooping to sin or following an unrighteous path, is obliged to return him toward the good, and to let him know that he is actually sinning against himself in pursuing wicked deeds for, it is said: "And thou shalt indeed rebuke thy neighbor" (Lev. 19.17). He who rebukes his fellow, whether it be regarding a sin committed between man and man, or whether it be regarding matters between man and God, it is essential that the rebuke be administered only between them both; and he shall speak to him calmly, employing soft language, telling him that he does not speak of it to him, save for his own good, to bring him to a life in the world to come. If he receive it attentively from him, it is well; if not, he should rebuke him a second, even a third time. So is the constant duty of a man to continue to rebuke his fellow, even until the sinner strike him, and say unto him: "I will not listen". He in whose power it is to prevent sin and does not take the means to prevent it, he himself is ultimately overtaken by their sin, since it was possible for him to prevent them.7Shabbat, 54a; Ibid. 119b; Baba Mezi’a 31a. C. G.