Yamim Tovimימים טובים

Spiritual Preparation for Yom Kippur

These sources outline the essential inner work and kavanos required to approach Yom Kippur with genuine teshuvah. They emphasize sincere remorse, reconciliation with others, abandonment of sin, verbal confession, and cultivating love of God alongside awe—forming a comprehensive framework for meaningful pre-Yom Kippur preparation.

אַף עַל פִּי שֶׁהַתְּשׁוּבָה וְהַצְּעָקָה יָפָה לָעוֹלָם, בַּעֲשָׂרָה הַיָּמִים שֶׁבֵּין רֹאשׁ הַשָּׁנָה וְיוֹם הַכִּפּוּרִים הִיא יָפָה בְּיוֹתֵר

7 sources · all verified

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Source 1 · Tanach
Verified

Isaiah – True Repentance and Fasting

Isaiah 57:14-58:8

God rejects hollow fasting and ritual while demanding genuine inner transformation — releasing injustice, feeding the hungry, and humbling the heart — as the true spiritual preparation that opens the gates of divine response.

כִּי֩ כֹ֨ה אָמַ֜ר רָ֣ם וְנִשָּׂ֗א שֹׁכֵ֥ן עַד֙ וְקָד֣וֹשׁ שְׁמ֔וֹ מָר֥וֹם וְקָד֖וֹשׁ אֶשְׁכּ֑וֹן וְאֶת־דַּכָּא֙ וּשְׁפַל־ר֔וּחַ לְהַחֲיוֹת֙ ר֣וּחַ שְׁפָלִ֔ים וּֽלְהַחֲי֖וֹת לֵ֥ב נִדְכָּאִֽים׃ הֲכָזֶ֗ה יִֽהְיֶה֙ צ֣וֹם אֶבְחָרֵ֔הוּ י֛וֹם עַנּ֥וֹת אָדָ֖ם נַפְשׁ֑וֹ הֲלָכֹ֨ף כְּאַגְמֹ֜ן רֹאשׁ֗וֹ וְשַׂ֤ק וָאֵ֙פֶר֙ יַצִּ֔יעַ הֲלָזֶה֙ תִּקְרָא־צ֔וֹם וְי֥וֹם רָצ֖וֹן לַיהֹוָֽה׃ הֲל֣וֹא זֶה֮ צ֣וֹם אֶבְחָרֵ֒הוּ֒ פַּתֵּ֙חַ֙ חַרְצֻבּ֣וֹת רֶ֔שַׁע הַתֵּ֖ר אֲגֻדּ֣וֹת מוֹטָ֑ה וְשַׁלַּ֤ח רְצוּצִים֙ חׇפְשִׁ֔ים וְכׇל־מוֹטָ֖ה תְּנַתֵּֽקוּ׃ הֲל֨וֹא פָרֹ֤ס לָרָעֵב֙ לַחְמֶ֔ךָ וַעֲנִיִּ֥ים מְרוּדִ֖ים תָּ֣בִיא בָ֑יִת כִּֽי־תִרְאֶ֤ה עָרֹם֙ וְכִסִּית֔וֹ וּמִבְּשָׂרְךָ֖ לֹ֥א תִתְעַלָּֽם׃

For thus said the One who high aloft Forever dwells, whose name is holy: I dwell on high, in holiness; Yet with the contrite and the lowly in spirit— Reviving the spirits of the lowly, Reviving the hearts of the contrite. Is such the fast I desire, A day for people to starve their bodies? Is it bowing the head like a bulrush And lying in sackcloth and ashes? Do you call that a fast, A day when GOD is favorable? No, this is the fast I desire: To unlock fetters of wickedness, And untie the cords of the yoke To let the oppressed go free; To break off every yoke. It is to share your bread with the hungry, And to take the wretched poor into your home; When you see the naked, to clothe them, And not to ignore your own kin.

Why it matters — The haftarah of Yom Kippur morning, this passage sets the foundational biblical vision of what Yom Kippur demands spiritually: authentic inner change, not mere ritual performance.

Source 2 · Chazal
Verified

Talmud Yoma – The Power of Yom Kippur and Teshuvah

Yoma 85b-86a

The Talmud discusses the atoning power of Yom Kippur and establishes that Yom Kippur does not atone for sins between a person and their fellow until reconciliation is made. R. Akiva's famous teaching that God Himself is Israel's purifier is also found here.

מַתְנִי׳ חַטָּאת וְאָשָׁם וַדַּאי — מְכַפְּרִין. מִיתָה וְיוֹם הַכִּפּוּרִים — מְכַפְּרִין עִם הַתְּשׁוּבָה. תְּשׁוּבָה — מְכַפֶּרֶת עַל עֲבֵירוֹת קַלּוֹת: עַל עֲשֵׂה, וְעַל לֹא תַעֲשֶׂה. וְעַל הַחֲמוּרוֹת הוּא תּוֹלֶה, עַד שֶׁיָּבֹא יוֹם הַכִּפּוּרִים וִיכַפֵּר. הָאוֹמֵר: אֶחֱטָא וְאָשׁוּב, אֶחֱטָא וְאָשׁוּב — אֵין מַסְפִּיקִין בְּיָדוֹ לַעֲשׂוֹת תְּשׁוּבָה. אֶחֱטָא וְיוֹם הַכִּפּוּרִים מְכַפֵּר — אֵין יוֹם הַכִּפּוּרִים מְכַפֵּר. עֲבֵירוֹת שֶׁבֵּין אָדָם לַמָּקוֹם — יוֹם הַכִּפּוּרִים מְכַפֵּר, עֲבֵירוֹת שֶׁבֵּין אָדָם לַחֲבֵירוֹ — אֵין יוֹם הַכִּפּוּרִים מְכַפֵּר, עַד שֶׁיְּרַצֶּה אֶת חֲבֵירוֹ. דָּרַשׁ רַבִּי אֶלְעָזָר בֶּן עֲזַרְיָה: ״מִכֹּל חַטֹּאתֵיכֶם לִפְנֵי ה׳ תִּטְהָרוּ״. עֲבֵירוֹת שֶׁבֵּין אָדָם לַמָּקוֹם — יוֹם הַכִּפּוּרִים מְכַפֵּר. עֲבֵירוֹת שֶׁבֵּין אָדָם לַחֲבֵירוֹ — אֵין יוֹם הַכִּפּוּרִים מְכַפֵּר עַד שֶׁיְּרַצֶּה אֶת חֲבֵירוֹ. אָמַר רַבִּי עֲקִיבָא: אַשְׁרֵיכֶם יִשְׂרָאֵל! לִפְנֵי מִי אַתֶּם מִטַּהֲרִין, מִי מְטַהֵר אֶתְכֶם? אֲבִיכֶם שֶׁבַּשָּׁמַיִם, שֶׁנֶּאֱמַר: ״וְזָרַקְתִּי עֲלֵיכֶם מַיִם טְהוֹרִים וּטְהַרְתֶּם״, וְאוֹמֵר: ״מִקְוֵה יִשְׂרָאֵל (ה׳)״, מָה מִקְוֶה מְטַהֵר אֶת הַטְּמֵאִים — אַף הַקָּדוֹשׁ בָּרוּךְ הוּא מְטַהֵר אֶת יִשְׂרָאֵל.

MISHNA: A sin-offering, which atones for unwitting performance of transgressions punishable by karet, and a definite guilt-offering, which is brought for robbery and misuse of consecrated items, atone for those sins. Death and Yom Kippur atone for sins when accompanied by repentance. Repentance itself atones for minor transgressions, for both positive mitzvot and negative mitzvot. And repentance places punishment for severe transgressions in abeyance until Yom Kippur comes and completely atones for the transgression. With regard to one who says: I will sin and then I will repent, I will sin and I will repent, Heaven does not provide him the opportunity to repent, and he will remain a sinner all his days. With regard to one who says: I will sin and Yom Kippur will atone for my sins, Yom Kippur does not atone for his sins. Furthermore, for transgressions between a person and God, Yom Kippur atones; however, for transgressions between a person and another, Yom Kippur does not atone until he appeases the other person. Similarly, Rabbi Elazar ben Azarya taught that point from the verse: “From all your sins you shall be cleansed before the Lord” (Leviticus 16:30). For transgressions between a person and God, Yom Kippur atones; however, for transgressions between a person and another, Yom Kippur does not atone until he appeases the other person. In conclusion, Rabbi Akiva said: How fortunate are you, Israel; before Whom are you purified, and Who purifies you? It is your Father in Heaven, as it is stated: “And I will sprinkle purifying water upon you, and you shall be purified” (Ezekiel 36:25). And it says: “The ritual bath of Israel is God” (Jeremiah 17:13). Just as a ritual bath purifies the impure, so too, the Holy One, Blessed be He, purifies Israel.

Why it matters — Establishes the core halakhic and spiritual framework for Yom Kippur: reconciliation with others must precede atonement from God, and the divine relationship is at the heart of the day's power.

Source 3 · Chazal
Verified

Talmud Yoma – Seeking Forgiveness Before Yom Kippur

Yoma 87b

The Talmud records that Rav would go to each person he may have wronged before Yom Kippur to ask forgiveness, and describes the proper manner of seeking and granting forgiveness in advance of the Day of Atonement.

תָּנוּ רַבָּנַן: מִצְוַת וִידּוּי עֶרֶב יוֹם הַכִּפּוּרִים עִם חֲשֵׁכָה. אֲבָל אָמְרוּ חֲכָמִים: יִתְוַדֶּה קוֹדֶם שֶׁיֹּאכַל וְיִשְׁתֶּה, שֶׁמָּא תִּטָּרֵף דַּעְתּוֹ בִּסְעוּדָה. וְאַף עַל פִּי שֶׁהִתְוַדָּה קוֹדֶם שֶׁאָכַל וְשָׁתָה — מִתְוַדֶּה לְאַחַר שֶׁיֹּאכַל וְיִשְׁתֶּה, שֶׁמָּא אֵירַע דְּבַר קַלְקָלָה בַּסְּעוּדָה. וְאַף עַל פִּי שֶׁהִתְוַדָּה עַרְבִית — יִתְוַדֶּה שַׁחֲרִית. שַׁחֲרִית — יִתְוַדֶּה בְּמוּסָף, בְּמוּסָף — יִתְוַדֶּה בְּמִנְחָה, בְּמִנְחָה — יִתְוַדֶּה בִּנְעִילָה. וְהֵיכָן אוֹמְרוֹ? יָחִיד אַחַר תְּפִלָּתוֹ, וּשְׁלִיחַ צִבּוּר אוֹמְרוֹ בָּאֶמְצַע. מַאי אָמַר? אָמַר רַב: ״אַתָּה יוֹדֵעַ רָזֵי עוֹלָם״. וּשְׁמוּאֵל אָמַר: ״מִמַּעֲמַקֵּי הַלֵּב״. וְלֵוִי אָמַר: ״וּבְתוֹרָתְךָ כָּתוּב לֵאמֹר״. רַבִּי יוֹחָנָן אָמַר: ״רִבּוֹן הָעוֹלָמִים״. רַבִּי יְהוּדָה אָמַר: ״כִּי עֲוֹנוֹתֵינוּ רַבּוּ מִלִּמְנוֹת וְחַטֹּאתֵינוּ עָצְמוּ מִסַּפֵּר״. רַב הַמְנוּנָא אָמַר: ״אֱלֹהַי, עַד שֶׁלֹּא נוֹצַרְתִּי אֵינִי כְּדַאי. עַכְשָׁיו שֶׁנּוֹצַרְתִּי, כְּאִילּוּ לֹא נוֹצַרְתִּי. עָפָר אֲנִי בְּחַיַּי, קַל וָחוֹמֶר בְּמִיתָתִי. הֲרֵי אֲנִי לְפָנֶיךָ כִּכְלִי מָלֵא בּוּשָׁה וּכְלִימָּה. יְהִי רָצוֹן מִלְּפָנֶיךָ שֶׁלֹּא אֶחֱטָא, וּמַה שֶׁחָטָאתִי — מְרוֹק בְּרַחֲמֶיךָ, אֲבָל לֹא עַל יְדֵי יִסּוּרִין״. וְהַיְינוּ וִידּוּיָא דְרָבָא כּוּלַּהּ שַׁתָּא, וּדְרַב הַמְנוּנָא זוּטָא בְּיוֹמָא דְכִפּוּרֵי.

§ The Sages taught: The main mitzva of confession is on Yom Kippur eve when darkness falls. But the Sages said: One should also confess on Yom Kippur eve before he eats and drinks at his last meal before the fast lest he become confused at the meal, due to the abundance of food and drink, and be unable to confess afterward. And although one confessed before he ate and drank, he confesses again after he eats and drinks, as perhaps he committed some sin during the meal itself. And although one confessed during the evening prayer on the night of Yom Kippur, he should confess again during the morning prayer. Likewise, although one confessed during the morning prayer, he should still confess during the additional prayer. Similarly, although one confessed during the additional prayer, he should also confess during the afternoon prayer; and although one confessed during the afternoon prayer, he should confess again during the closing prayer [ne’ila]. And where in the Yom Kippur prayers does one say the confession? An individual says it after his Amida prayer, and the prayer leader says it in the middle of the Amida prayer. The Gemara asks: What does one say; what is the liturgy of the confession? Rav said: One says the prayer that begins: You know the mysteries of the universe, in accordance with the standard liturgy. And Shmuel said that the prayer begins with: From the depths of the heart. And Levi said that it begins: And in your Torah it is written, saying, and one then recites the forgiveness achieved by Yom Kippur as stated in the Torah. Rabbi Yoḥanan said that it begins: Master of the Universe. Rabbi Yehuda said that one says: For our iniquities are too many to count and our sins are too great to number. Rav Hamnuna said: This is the liturgy of the confession: My God, before I was formed I was unworthy. Now that I have been formed, it is as if I had not been formed. I am dust while alive, how much more so when I am dead. See, I am before You like a vessel filled with shame and disgrace. May it be Your will that I may sin no more, and as for the sins I have committed before You, erase them in Your compassion, but not by suffering. The Gemara comments: This is the confession that Rava used all year long; and it was the confession that Rav Hamnuna Zuta used on Yom Kippur.

Why it matters — Directly prescribes the interpersonal spiritual preparation essential before Yom Kippur — seeking forgiveness from those one has wronged.

Source 4 · Rishonim
Verified

Rambam – Hilchot Teshuvah, Definition and Components

Mishneh Torah, Repentance 2:1-7

Rambam defines teshuvah as abandoning the sin, removing it from one's thoughts, and resolving never to repeat it — accompanied by verbal confession (viduy). He stresses that complete teshuvah is demonstrated when one faces the same situation and chooses differently.

אַף עַל פִּי שֶׁהַתְּשׁוּבָה וְהַצְּעָקָה יָפָה לָעוֹלָם. בַּעֲשָׂרָה הַיָּמִים שֶׁבֵּין רֹאשׁ הַשָּׁנָה וְיוֹם הַכִּפּוּרִים הִיא יָפָה בְּיוֹתֵר וּמִתְקַבֶּלֶת הִיא מִיָּד שֶׁנֶּאֱמַר (ישעיה נה ו) "דִּרְשׁוּ ה' בְּהִמָּצְאוֹ". בַּמֶּה דְּבָרִים אֲמוּרִים בְּיָחִיד אֲבָל צִבּוּר כָּל זְמַן שֶׁעוֹשִׂים תְּשׁוּבָה וְצוֹעֲקִין בְּלֵב שָׁלֵם הֵם נַעֲנִין שֶׁנֶּאֱמַר (דברים ד ז) "כַּה' אֱלֹהֵינוּ בְּכָל קָרְאֵנוּ אֵלָיו": יוֹם הַכִּפּוּרִים הוּא זְמַן תְּשׁוּבָה לַכּל לַיָּחִיד וְלָרַבִּים וְהוּא קֵץ מְחִילָה וּסְלִיחָה לְיִשְׂרָאֵל. לְפִיכָךְ חַיָּבִים הַכּל לַעֲשׂוֹת תְּשׁוּבָה וּלְהִתְוַדּוֹת בְּיוֹם הַכִּפּוּרִים. וּמִצְוַת וִדּוּי יוֹם הַכִּפּוּרִים שֶׁיַּתְחִיל מֵעֶרֶב הַיּוֹם קֹדֶם שֶׁיֹּאכַל שֶׁמָּא יֵחָנֵק בַּסְּעֻדָּה קֹדֶם שֶׁיִּתְוַדֶּה. וְאַף עַל פִּי שֶׁהִתְוַדָּה קֹדֶם שֶׁיֹּאכַל חוֹזֵר וּמִתְוַדֶּה בְּלֵילֵי יוֹם הַכִּפּוּרִים עַרְבִית וְחוֹזֵר וּמִתְוַדֶּה בְּשַׁחֲרִית וּבְמוּסָף וּבְמִנְחָה וּבִנְעִילָה. וְהֵיכָן מִתְוַדֶּה. יָחִיד אַחַר תְּפִלָּתוֹ וּשְׁלִיחַ צִבּוּר בְּאֶמְצַע תְּפִלָּתוֹ בִּבְרָכָה רְבִיעִית:

Even though repentance and calling out [to God] are desirable at all times, during the ten days between Rosh HaShanah and Yom Kippur, they are even more desirable and will be accepted immediately as [Isaiah 55:6] states: "Seek God when He is to be found." When does the above apply? To an individual. However, in regard to a community, whenever they repent and cry out wholeheartedly, they are answered immediately as [Deuteronomy 4:7] states: "[What nation is so great that they have God close to them,] as God, our Lord, is whenever we call Him." Yom Kippur is the time of Teshuvah for all, both individuals and the community at large. It is the apex of forgiveness and pardon for Israel. Accordingly, everyone is obligated to repent and confess on Yom Kippur. The mitzvah of the confession of Yom Kippur begins on the day's eve, before one eats [the final meal], lest one choke to death in the meal before confessing. Although a person confessed before eating, he should confess again in the evening service, Yom Kippur night, and similarly, repeat the confession in the morning, Musaf, afternoon, and Ne'ilah services. At which point [in the service] should one confess? An individual confesses after the Amidah and the Chazan confesses in the midst of the Amidah, in the fourth blessing.

Why it matters — The Rambam's systematic account of what genuine inner preparation for Yom Kippur looks like, including the structure of viduy that forms the backbone of the day's liturgy.

Source 5 · Rishonim
Verified

Sha'arei Teshuvah (Rabbeinu Yonah) – The Components of Teshuvah

Sha'arei Teshuvah 2:1-14

Rabbeinu Yonah enumerates twenty components of genuine teshuvah, including regret (charatah), abandonment of sin (azivat ha-chet), verbal confession (viduy), and acceptance not to repeat the sin — forming the definitive Rishon framework for pre-Yom Kippur spiritual preparation.

הַשַּׁעַר הַשֵּׁנִי – לְהוֹרוֹת הַדְּרָכִים שֶׁיִּתְעוֹרֵר הָאָדָם בָּהֶם לָשׁוּב אֶל ה'. דַּע כִּי דַּרְכֵי הַסִּבּוֹת שֶׁיִּתְעוֹרֵר הָאָדָם בָּהֶם לָשׁוּב מִדְּרָכָיו הָרָעִים שִׁשָּׁה. וּבְכָל אֶחָד מֵהֶם לִמַּדְנוּ דַּעַת אֶת הָאָדָם אֵיךְ יִתְחַלֵּק בְּחֵקֶר תְּבוּנָתוֹ. וְיַאֲזִין עַד תְּכוּנָתוֹ. וְנָעִיר לָהֶם אֹזֶן לִשְׁמֹעַ. הַשְׂכֵּל וְיָדוֹעַ. עִקָּרִים יְקָרִים. לְכָל חֶפְצֵיהֶם דְּרוּשִׁים נֶחְקָרִים. וְיֹתֵר מֵהֵמָּה בְּנִי הִזָּהֵר. לָשׁוּב בְּכָל יוֹם וְנַפְשְׁךָ לְטַהֵר. בִּלְעֲדֵי תֶּחֱזֶה סִבָּה מְעוֹרֶרֶת וְיַלְדֵי יוֹם יְקֹשׁוּן מַחְשְׁבוֹתֶיךָ. כִּי תִּזְכֹּר אֶת בּוֹרְאֶךָ. וְהָיָה לְךָ זִכְרוֹ לְמֵשִׁיב נֶפֶשׁ מִדַּרְכֵי תּוֹלְדוֹת גּוּשׁ עָפָר. וּבְכֵן עֶרְיָה תֵּעוֹר קֶשֶׁת מַדָּע לְיַשֵּׁר הֲדוּרֵי טִבְעֲךָ. וּמִיִּרְאַת הַשֵּׁם וְאַהֲבָתוֹ וְהַבּוּשָׁה מִלְּפָנָיו תּוֹסִיף מַעֲלָה תָּמִיד. וְתִשְׁקֹד עַל נִקְיוֹן כַּפֶּיךָ וּכְרֹת רַעֲיוֹנִים מוֹרְדִים מִשַּׂרְעַפֶּיךָ. וְהִבָּרוּ נוֹשְׂאֵי כְּלֵי נַפְשֶׁךָ. וּבְזָכְרָהּ יוֹצְרָהּ תַּעְדֶּה עֶדְיָהּ וְתִכְלֹל יָפְיָהּ כמש"כ (ישעיהו מ"ה:כ"ה) בַּה' יִצְדְּקוּ וְיִתְהַלְלוּ כָּל זֶרַע יִשְׂרָאֵל. וְתוֹסִיף אֹמֶץ לְהָעִיר אֶת רוּחֲךָ בְּדַרְכֵי הַסִּבּוֹת הַשִּׁשָּׁה אֲשֶׁר יִתְבָּאֲרוּ. וַאֲשֶׁר לֹא הִשִּׂיג הַמַּעֲלָה הַזֹּאת יִכָּנַע לְבָבוֹ הֶעָרֵל מִדֶּרֶךְ הַסִּבּוֹת וְרָאוֹת רַבּוֹת. וּלְפִי מִעוּט הַהַכָּרָה מִדֶּרֶךְ הַסִּבָּה הַמְּעוֹרֶרֶת לֵב הָאָדָם לִתְשׁוּבָה. וּכְפִי נְטוֹתָהּ אֶל דֶּרֶךְ הָרָצוֹן יִוָּדַע וְיִבָּחֵן כִּי הַתְּשׁוּבָה. מִן הַנֶּפֶשׁ הַחֲשׁוּבָה. הַדֶּרֶךְ הַחֲמִישִׁית – בַּעֲשֶׂרֶת יְמֵי תְּשׁוּבָה. הַיָּרֵא אֶת דְּבַר הַשֵּׁם לִבּוֹ יָחִיל בְּקִרְבּוֹ בְּדַעְתּוֹ שֶׁכָּל מַעֲשָׂיו בַּסֵּפֶר נִכְתָּבִין. וּבָעֵת הַהִיא הָאֱלֹקִים יָבִיא בְמִשְׁפָּט אֶת כָּל מַעֲשֶׂה עַל כָּל נֶעְלָם אִם טוֹב וְאִם רָע. כִּי הָאָדָם נִדּוֹן בְּרֹאשׁ הַשָּׁנָה וּגְזַר דִּין שֶׁלּוֹ נֶחְתָּם בְּיוֹם הַכִּפּוּרִים. וּבְעֵת אֲשֶׁר יֵדַע כִּי יָבִיאוּ אֶת דִּינוֹ לִפְנֵי מֶלֶךְ בָּשָׂר וָדָם הֲלֹא יֶחֱרַד חֲרָדָה גְּדוֹלָה וְיָשִׁית עֵצוֹת בְּנַפְשׁוֹ וּבְכָל דַּרְכֵי חֲרִיצוּת יָחִישׁ מִפְלָט לוֹ. וְלֹא תַּעֲלֶה עַל רוּחוֹ לִפְנוֹת עַל יָמִין אוֹ עַל שְׂמֹאל וּלְהִתְעַסֵּק בְּיֶתֶר חֲפָצָיו. וְלֹא יַשְׁגִּיחַ לְפַתֵּחַ וּלְשַׂדֵּד אַדְמָתוֹ וְלֹא יִפְנֶה דֶּרֶךְ כְּרָמִים. וְלֹא יִתְרַפֶּה בְּיוֹם צָרָה מֵהָכִין לֵב לְהִנָּצֵל כִּצְבִי מִיָּד. לָכֵן מָה נוֹאֲלוּ הַיּוֹצְאִים לְפָעֳלָם וְלַעֲבוֹדָתָם עֲדֵי עָרֶב בַּיָּמִים הַנּוֹרָאִים יְמֵי הַדִּין וְהַמִּשְׁפָּט וְאֵינָם יוֹדְעִים מָה יִהְיֶה מִשְׁפָּטָם. הֲלֹא לְהָגוּתָם יֶהְגֶּה לִבָּם בַּיּוֹם שֶׁיְּדֻבַּר בָּם שֶׁנֶּאֱמַר (שיר השירים ח':ח') מַה נַּעֲשֶׂה לַאֲחוֹתֵנוּ בַּיּוֹם שֶׁיְּדֻבַּר בָּהּ. וְרָאוּי לְכָל יְרֵא אֱלֹהִים לְמַעֵט בַּעֲסָקָיו לִהְיוֹת רַעְיוֹנָיו נְחִתִּים. וְלִקְבֹּעַ בַּיּוֹם וּבַלַּיְלָה עִתִּים לְהִתְבּוֹדֵד בַּחֲדָרָיו וּלְחַפֵּשׂ דְּרָכָיו וְלַחְקֹר. וּלְקַדֵּם אַשְׁמוּרוֹת וּלְהִתְעַסֵּק בְּדַרְכֵי הַתְּשׁוּבָה וְכִשְׁרוֹן הַמַּעֲשֶׂה. וְלִשְׁפֹּךְ שִׁיחַ וְלָשֵׂאת תְּפִלָּה וְרִנָּה. וּלְהַפִּיל תְּחִנָּה. וְהָעֵת עֵת רָצוֹן וְהַתְּפִלָּה נִשְׁמַעַת בּוֹ כָּעִנְיָן שֶׁנֶּאֱמַר (ישעיה מ"ט:ח') בְּעֵת רָצוֹן עֲנִיתִיךָ וּבְיוֹם יְשׁוּעָה עֲזַרְתִּיךָ. וְאָמְרוּ רַבּוֹתֵינוּ זִכְרוֹנָם לִבְרָכָה (ר"ה יח.) דִּרְשׁוּ ה' בְּהִמָּצְאוֹ אֵלּוּ עֲשָׂרָה יָמִים שֶׁבֵּין רֹאשׁ הַשָּׁנָה לְיוֹם הַכִּפּוּרִים. וּמִצְוַת עֲשֵׂה מִן הַתּוֹרָה לְהָעִיר אָדָם אֶת רוּחוֹ לַחְזֹר בִּתְשׁוּבָה בְּיוֹם הַכִּפּוּרִים שֶׁנֶּאֱמַר (ויקרא ט"ז:ל') מִכֹּל חַטֹּאתֵיכֶם לִפְנֵי ה' תִּטְהָרוּ. עַל כֵּן הִזְהִירָנוּ הַכָּתוּב שֶׁנִּטְהַר לִפְנֵי ה' בִּתְשׁוּבָתֵנוּ וְהוּא יְכַפֵּר עָלֵינוּ בַּיּוֹם הַזֶּה לְטַהֵר אוֹתָנוּ.

To instruct about the ways that arouse a person to repent to God Know that the paths of the causes by which a person is aroused to repent from his evil ways are six. And with each one of them, we have taught man's intellect how it is dissected for his understanding; so let him give ear according to his preparation. And we will arouse the ear to understand them, to contemplate and know the precious principles - they are expounded and analyzed to all of their wants. But more than this, my son, be careful to repent and purify your soul each day - [even] without seeing a cause that arouses [it] or the events of the day striking your thoughts. For remember your Creator, and let the thought of Him be a restoration of the soul from the ways of the events of [those who are only] a clod of dirt. And so bare and prepare the bow of knowledge to straighten the refinements of your nature. And from the fear of God and love of Him, and from the shame [of being] before him, you will always increase virtue. [Also] be consistent in the purity of your hands, cut down the rebellious thoughts from your musings and feed the arms bearers of your soul - and with the remembrance of its Former, it will adorn its jewelry and be complete in its beauty, as it is written (Isaiah 45:25), "It is through the Lord that all the offspring of Israel Have vindication and praise." However add strength to arouse your soul with these six causes which will be explained. And the one who does not grasp this virtue will surrender his uncircumcised heart from the way of the causes and from much seeing. And according to the paucity of the recognition of the way of a cause that arouses the heart of a man to repent - and according to his veering to the path of his [own] will - is it made known and verified that repentance is from the important soul. The fifth path is [that] on the ten days of repentance, the heart of one who fears the Lord will pine inside himself, knowing in his mind that all of his deeds are written in a book and that at that time, God brings all of His creation to judgement about all that is hidden - whether for the good or for the bad. For man is judged on Rosh Hashanah and his final verdict is sealed on Yom Kippur. And at a time that he knows that they will bring his case in front of a king of flesh and blood, does he not tremble greatly, seek counsel for himself and scurry industriously to find a way to escape? And it does not come to his spirit to turn to the right or to the left or to occupy himself with the rest of his business. And he will not break up and furrow his land nor turn through the vineyards. And on a day of distress, he will not falter from preparing his heart to escape like a deer from the hand [of the hunter]. Therefore how foolish are those who go out to their labors and their work until the evening on the Days of Awe - days of judgement and verdict - and do not know what their verdict will be. Is it not that their hearts are preoccupied [even] about their sister on the day when she will be spoken for - as it is stated (Song of Songs 8:8), "What shall we do for our sister when she is spoken for?" And it is fitting for anyone that fears God to reduce his affairs, so that his ideas are at ease; to fix times during the day and night to seclude himself in his rooms, search his ways and investigate; to be early to the watches and occupy himself with the ways of repentance and the refinement of action; and to pour out speech, raise prayer and song and to lay down supplication. And this time is a time of [good] will, and prayer will be heard on it - like the matter that is stated (Isaiah 49:8), "In an hour of favor I answer you, and on a day of salvation I help you." And our Rabbis, may their memory be blessed, said (Rosh Hashanah 18a), "'Seek the Lord while He can be found' - these are the ten days between Rosh Hashanah and Yom Kippur." And it is a positive commandment from the Torah for a man to arouse his spirit to repent on Yom Kippur, as it is stated (Leviticus 16:30), "of all your sins, you shall be pure before the Lord." Therefore Scripture warned us that we should purify ourselves before God with our repentance; and He will atone for us on that day to purify us.

Why it matters — The essential Rishon guide for how to prepare one's teshuvah before Yom Kippur, specifying exactly which inner acts and intentions constitute real repentance.

Source 6 · Rishonim
Verified

Chovot HaLevavot – Inner Conditions of Teshuvah

Duties of the Heart, Seventh Treatise on Repentance.3

Rabbeinu Bachya outlines the inner spiritual conditions for teshuvah: sincere remorse in the heart, not just on the lips; genuine intention to change; and the importance of approaching God with humility and love rather than fear alone.

הָרִאשׁוֹן שֶׁיֵּדַע גְּנוּת מַעֲשֵׂהוּ יְדִיעָה בְּרוּרָה כִּי אִם לֹא יִתְבָּרֵר לוֹ זֶה וְיִהְיֶה מִסְתַּפֵּק אוֹ שׁוֹגֵג בִּלְתִּי מֵזִיד לֹא תִּתָּכֵן הַחֲרָטָה מִמֶּנּוּ עָלָיו וּבַקָּשַׁת הַמְּחִילָה בּוֹ כְּמוֹ שֶׁכָּתוּב (תהלים נא) כִּי פְשָׁעַי אֲנִי אֵדָע וְחַטָּאתִי נֶגְדִּי תָמִיד. וְהַשֵּׁנִי שֶׁיֵּדַע בְּחִיּוּב רֹעַ מַעֲשֵׂהוּ וּגְנוּתוֹ כִּי אִם לֹא יִתְבָּרֵר אֶצְלוֹ כִּי מַעֲשֵׂהוּ רַע וּמִפְעָלוֹ אֵינוֹ טוֹב לֹא יִתְחָרֵט עָלָיו וְלֹא יְקַבֵּל תְּנָאֵי הַתְּשׁוּבָה מִמֶּנּוּ וְדִינוֹ בּוֹ כְּדִין הַשּׁוֹגֵג וַאֲמַתְלָאָתוֹ רְחָבָה כמ״ש (שם יט) שְׁגִיאוֹת מִי יָבִין וְגוֹ׳. וְהַשְּׁבִיעִי חֹזֶק סִבְלוֹ לְהִמָּנַע מִן הָרַע אֲשֶׁר הִרְגִּיל בּוֹ וְהַסְכָּמָתוֹ לָסוּר מִמֶּנּוּ בְּלִבּוֹ וּבְמַצְפּוּנוֹ כְּמוֹ שֶׁכָּתוּב (יואל ב) וְקִרְעוּ לְבַבְכֶם וְאַל בִּגְדֵיכֶם.

(1) The penitent must understand clearly that he did a disgraceful act. Because, if this is not clear to him, and he is in doubt or ignorant of it, it is not possible for him to regret it and seek forgiveness for it, as written: "For I know my transgressions, and my sin is ever before me" (Tehilim 51:5) (2) He must understand the gravity of his sin and its disgracefulness, since if it is not clear to him that his deed was evil, he will not regret it nor take on the conditions of repentance for it. He will imagine that his act is like unintentional and that he will easily be able to justify himself, as written: "But who can discern their own errors? Forgive my hidden faults" (Tehilim 19:13). (7) He must strengthen himself greatly to be able to bear the suffering from refraining to do the evil he had been addicted to do, and firmly resolve inwardly and outwardly to renounce it, as written "And tear your hearts, and not your garments" (Yoel 2:13).

Why it matters — Deepens the spiritual preparation for Yom Kippur by insisting that the kavana must be fully internalized — teshuvah of the heart, not merely of the mouth.

Source 7 · Hasidic
Verified

Kedushat Levi – Teshuvah from Love

Kedushat Levi, Deuteronomy, For Rosh HaShanah 1

Reb Levi Yitzchak of Berditchev teaches that the highest form of teshuvah is driven by ahavah — love of God — rather than fear, and that on the Days of Awe one should stand before God with joy and confidence in divine love, not only with fear and trembling.

הכלל הוא, כי בראש חודש אלול השם יתברך מגלה אלהותו ומלכותו לנשמת ישראל וכי הוא מנהיג את כל העולמות בחסדו הגדול וישראל עם קדושו ממליכים עול מלכותו עליהם. וזהו אדקטיר לו לבר קטיר ספינתך, בשעה שאתה קושר לבך לעבדו קטיר ספינתך תקשור על זו המדריגה שבראש חודש אלול מגלה השם יתברך לנשמת ישראל, כי הוא מנהיג העולם.

Why it matters — A key Chassidic kavana for Yom Kippur: approaching the day with love and simcha alongside awe, transforming the day from one of dread into one of intimate divine encounter.