Yamim Tovimימים טובים

Spiritual Preparation and Kavana for Yom Kippur

These sources address the inner and outer dimensions of preparing for Yom Kippur, from Talmudic teachings on proper prayer mindfulness to comprehensive treatments of repentance (teshuva) by medieval and early modern authorities. They emphasize genuine remorse, self-examination, interpersonal reconciliation, and the transformation of heart required to approach the Day of Atonement.

אָמְנָם עַל דֶּרֶךְ פְּרָט הַמֵּבִיא לָזֶה, הוּא הַהִתְבּוֹנְנוּת עַל חֹמֶר הָעֲבוֹדָה

7 sources · verified

Opens as a working sheet — explore, annotate, and export.

Source 1 · Chazal
Verified

Talmud Berakhot 30a

Berakhot 30a

The Talmud teaches that one should not stand to pray in a state of levity or frivolity, but rather with the gravity (koved rosh) that comes from reflecting on the weight of halacha; the pious of earlier generations would spend an hour preparing their hearts before prayer.

לִישַׁתֵּף אִינָשׁ נַפְשֵׁיהּ בַּהֲדֵי צִבּוּרָא. הֵיכִי נֵימָא? — ״יְהִי רָצוֹן מִלְּפָנֶיךָ ה׳ אֱלֹהֵינוּ שֶׁתּוֹלִיכֵנוּ לְשָׁלוֹם״ וְכוּ׳. הָיָה עוֹמֵד בְּחוּץ לָאָרֶץ — יְכַוֵּין אֶת לִבּוֹ כְּנֶגֶד אֶרֶץ יִשְׂרָאֵל, שֶׁנֶּאֱמַר: ״וְהִתְפַּלְלוּ אֵלֶיךָ דֶּרֶךְ אַרְצָם״. הָיָה עוֹמֵד בְּאֶרֶץ יִשְׂרָאֵל — יְכַוֵּין אֶת לִבּוֹ כְּנֶגֶד יְרוּשָׁלַיִם, שֶׁנֶּאֱמַר: ״וְהִתְפַּלְלוּ אֶל ה׳ דֶּרֶךְ הָעִיר אֲשֶׁר בָּחַרְתָּ״. הָיָה עוֹמֵד בִּירוּשָׁלַיִם — יְכַוֵּין אֶת לִבּוֹ כְּנֶגֶד בֵּית הַמִּקְדָּשׁ, שֶׁנֶּאֱמַר: ״וְהִתְפַּלְלוּ אֶל הַבַּיִת הַזֶּה״. הָיָה עוֹמֵד בְּבֵית הַמִּקְדָּשׁ — יְכַוֵּין אֶת לִבּוֹ כְּנֶגֶד בֵּית קׇדְשֵׁי הַקֳּדָשִׁים, שֶׁנֶּאֱמַר: ״וְהִתְפַּלְלוּ אֶל הַמָּקוֹם הַזֶּה״. הָיָה עוֹמֵד בְּבֵית קׇדְשֵׁי הַקֳּדָשִׁים — יְכַוֵּין אֶת לִבּוֹ כְּנֶגֶד בֵּית הַכַּפּוֹרֶת. הָיָה עוֹמֵד אֲחוֹרֵי בֵּית הַכַּפּוֹרֶת — יִרְאֶה עַצְמוֹ כְּאִילּוּ לִפְנֵי הַכַּפּוֹרֶת. נִמְצָא עוֹמֵד בַּמִּזְרָח מַחֲזִיר פָּנָיו לַמַּעֲרָב. בַּמַּעֲרָב מַחֲזִיר פָּנָיו לַמִּזְרָח. בַּדָּרוֹם — מַחֲזִיר פָּנָיו לַצָּפוֹן. בַּצָּפוֹן — מַחֲזִיר פָּנָיו לַדָּרוֹם. נִמְצְאוּ כׇּל יִשְׂרָאֵל מְכַוְּונִין אֶת לִבָּם לְמָקוֹם אֶחָד.

a person should associate himself with the congregation and should not pray for himself alone. How should he say it? May it be Your will, Lord our God, that You lead us to peace, etc., in the plural. One who was standing in prayer in the Diaspora should focus his heart toward Eretz Yisrael, as it is stated: “And they shall pray to You by way of their land which You have given to their fathers” (I Kings 8:48). One who was standing in Eretz Yisrael should focus his heart toward Jerusalem, as it is stated: “And they shall pray to the Lord by way of the city that You have chosen” (I Kings 8:44). One who was standing in Jerusalem should focus his heart toward the Temple, as it is stated: “And they shall pray toward this house” (II Chronicles 6:32). One who was standing in the Temple should focus his heart toward the Holy of Holies, as it is stated: “And they shall pray toward this place” (I Kings 8:35). One who was standing in the Holy of Holies should focus his heart toward the seat of the ark-cover [kapporet], atop the ark, the dwelling place of God’s glory. One who was standing behind the seat of the ark-cover should visualize himself as if standing before the ark-cover and turn toward it. Consequently, one standing in prayer in the East turns to face west, and one standing in the West turns to face east. One standing in the South turns to face north, and one standing in the North turns to face south; Consequently, all of the people of Israel focus themselves focusing their hearts toward one place, the Holy of Holies in the Temple.

Why it matters — Establishes the principle of pre-prayer preparation (hitbonenut and koved rosh) that applies with special force on Yom Kippur.

Source 2 · Rishonim
Verified

Rambam, Hilchot Teshuva

Mishneh Torah, Repentance 2:1-7

The Rambam defines teshuva as consisting of: abandoning the sin, resolving never to repeat it, and verbal confession. He emphasizes that teshuva requires genuine inner transformation — that one's mindset and self-conception must change, not just external behavior.

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 definition of teshuva provides the halakhic and philosophical framework for understanding what kavanos are required when doing viduy on Yom Kippur.

Source 3 · Rishonim
Verified

Sha'arei Teshuva — Rabbeinu Yona

Sha'arei Teshuvah 2:7-10

Rabbeinu Yona details the components of complete teshuva: remorse (charata), verbal confession (viduy), abandonment of sin, and resolution not to repeat it. He emphasizes that teshuva must be done with a full heart, and lists the Ten Days of Repentance as especially propitious for completing this process.

וְיֵשׁ אֲנָשִׁים רַבִּים יִמָּנַע מֵהֶם אוֹר הַתְּשׁוּבָה. כִּי הֵם זַכָּאִים וּטְהוֹרִים בְּעֵינֵיהֶם וְלֹא יִתְעַשְּׁתוּ עַל תִּקּוּן מַעֲשֵׂיהֶם. כִּי דִּמּוּ בְּנַפְשָׁם שֶׁהֵם מְתֻקָּנִים וְהֵם חַטָּאִים לַה' מְאֹד. הֲלֹא כָּתוּב (קהלת ז':כ') כִּי אָדָם אֵין צַדִּיק בָּאָרֶץ אֲשֶׁר יַעֲשֶׂה טּוֹב וְלֹא יֶחֱטָא. וְהָאֲנָשִׁים הָהֵם מֵאֲשֶׁר הֵם בּוֹזִים לִדְבַר עֲוֹנוֹת. לֹא יַרְגִּישׁוּ וְלֹא יָבִינוּ לְמוֹ. אוֹ הוֹדַע אֲלֵיהֶם חַטָּאתָם וְנִשְׁכַּח מִלִּבָּם אַחֲרֵי כֵן. וְהִנָּם כְּמוֹ הַחוֹלֶה שֶׁאֵינוֹ מַרְגִּישׁ בְּחָלְיוֹ וְלֹא יַחְשֹׁב עַל הָרְפוּאָה וְיִכְבַּד חָלְיוֹ תָּמִיד עַד אֲשֶׁר לֹא יוּכַל לְהֵרָפֵא. וּפְעָמִים תִּהְיֶה נְסִבָּה לָזֹאת מִקֹּצֶר בִּינָתָם. כִּי לֹא יָבֹאוּ לִדְרֹשׁ אֱלֹהִים וְדַעַת דְּרָכָיו לֹא יֶחְפָּצוּן. עַל כֵּן לֹא יִשְׁקְדוּ עַל דַּלְתוֹת חֲכָמִים וְתַלְמִידִים. כָּעִנְיָן שֶׁנֶּאֱמַר (משלי ט"ו:י"ב) לֹא יֶאֱהַב לֵץ הוֹכֵחַ לוֹ אֶל חֲכָמִים לֹא יֵלֵךְ. וְהִנֵּה אֲנָשִׁים צַדִּיקִים וִישָׁרִים בְּלִבּוֹתָם. שְׁאָגָה לָהֶם כַּלָּבִיא תָּמִיד בְּמַחְשְׁבוֹתָם. וְיִנְהֲמוּ עַל חֲטָאֵיהֶם כְּנַהֲמַת יָם. וְעַל אֲשֶׁר קָצוֹר קָצְרָה יָדָם מֵעֲבוֹדַת הַשֵּׁם. כִּי עַל זֶה יִפְשַׁע גֶּבֶר וְהִרְבָּה אַשְׁמָה כְּמוֹ עַל הָעֲבֵרוֹת הַחֲמוּרוֹת. כָּעִנְיָן שֶׁאָמְרוּ רַבּוֹתֵינוּ זִכְרוֹנָם לִבְרָכָה וִתֵּר הקב"ה עַל גִּלּוּי עֲרָיוֹת וְעַל שְׁפִיכוּת דָּמִים וְלֹא וִתֵּר לַעֲוֹן בִּטּוּל תּוֹרָה. אַף כִּי מָלְאוּ רַע הָאֲנָשִׁים אֲשֶׁר עִקַּר מַחְשְׁבוֹתֵיהֶם וּמַעֲשֵׂיהֶם עַל חֶפְצֵי גּוּפָם וְהַבְלֵי זְמַנָּם. וּבְסוֹד הַיִּרְאָה אַל תָּבֹא נַפְשָׁם. וּלְהִשְׁתּוֹנֵן כִּלְיוֹתָם עָלֶיהָ אַל תֵּחַד כְּבוֹדָם בְּמַשְׂכִּיּוֹת לְבָבָם וְחַדְרָם וּמַשְׂכִּיֹּתָם לְעִתִּים מְזֻמָּנִים. וְלֹא יִתְּנוּ חֵלֶק לַתּוֹרָה בְּעִסְקֵיהֶם. וּמִקֶּרֶב לִבָּם אָבַד חֶשְׁבּוֹן עַל נַפְשָׁם. כִּי גוֹי אֹבַד עֵצוֹת הֵמָּה. וְכַמָּה הֵם בְּמַדְרֵגָה תַּחְתּוֹנָה. וְאָמְרוּ רַבּוֹתֵינוּ זִכְרוֹנָם לִבְרָכָה בֶּן שִׁשִּׁים שָׁנָה לַזִּקְנָה בֶּן שִׁבְעִים לַשֵּׂיבָה בֶּן שְׁמֹנִים לַגְּבוּרָה בֶּן תִּשְׁעִים לָשׂוּחַ בֶּן מֵאָה כְּאִלּוּ מֵת וְעָבַר וּבָטֵל מִן הָעוֹלָם. וְהָיְתָה כַּוָּנָתָם זַ"ל בַּדְּבָרִים הָאֵלֶּה לְהַזְהִיר עַל הַתְּשׁוּבָה. וְשֶׁיַּחְשֹׁב הָאָדָם עַל קִצּוֹ בְּהַגִּיעוֹ לִימֵי הַזִּקְנָה. אִם לֹא זָכָה לַעֲשׂוֹת כֵּן בִּימֵי בְּחוּרוֹתָיו. וְאַחֲרֵי כִּי קָרוֹב לָבֹא עִתּוֹ יַעֲזֹב חֶפְצֵי הַגּוּף וְתַאֲווֹתָיו וִיתַקֵּן נַפְשׁוֹ. וּבְהַגִּיעַ לִימֵי הַשֵּׂיבָה יוֹסִיף לְגָרֵשׁ מִלִּבּוֹ עִנְיַן הָעוֹלָם. וּלְפִי מִעוּט הַשָּׁנִים הַבָּאוֹת יַמְעִיט בְּעֵסֶק הָעוֹלָם וְיִתְיַחֵד תָּמִיד לְהִתְבּוֹנֵן בְּיִרְאַת הַשֵּׁם. וְלַחְשֹׁב עִם נַפְשׁוֹ וּלְתַקֵּן מִדּוֹתָיו. וּלְבַקֵּשׁ תּוֹרָה וּמִצְוֹת. וּמָה שֶׁאָמְרוּ בֶּן תִּשְׁעִים לָשׂוּחַ הוּא מִלְּשׁוֹן (תהילים ק"ב:א') יִשְׁפֹּךְ שִׂיחוֹ (בראשית כ"ד:ס"ג) לָשׂוּחַ בַּשָּׂדֶה. כְּמוֹ שֶׁפֵּרְשׁוּ רַבּוֹתֵינוּ זִכְרוֹנָם לִבְרָכָה יִצְחָק תִּקֵּן תְּפִלַּת הַמִּנְחָה שֶׁנֶּאֱמַר וַיֵּצֵא יִצְחָק לָשׂוּחַ בַּשָּׂדֶה. כִּי אַחֲרֵי שֶׁהִגִּיעַ לְתִשְׁעִים רָאוּי לוֹ לִהְיוֹת כָּל עִסְקוֹ בִּתְפִלּוֹת וּבִתְהִלּוֹת הַשֵּׁם וְלָשִׂיחַ בְּנִפְלְאוֹתָיו. וְדִבֵּר שְׁלֹמֹה הַמֶּלֶךְ עָלָיו הַשָּׁלוֹם בְּעִנְיַן יְמֵי הַזִּקְנָה שֶׁלֹּא יִתְעַצֵּל הָאָדָם בָּהֶם מֵעֲבוֹדַת הש"י וְאָמַר (קהלת י"א:ו') בַּבֹּקֶר זְרַע אֶת זַרְעֶךָ וְלָעֶרֶב אַל תַּנַּח יָדֶךָ כִּי אֵינְךָ יוֹדֵעַ אֵי זֶה יִכְשָׁר הֲזֶה אוֹ זֶה וְאִם שְׁנֵיהֶם כְּאֶחָד טוֹבִים. הִמְשִׁיל יְמֵי הַיַּלְדוּת וְהַשַּׁחֲרוּת לַבֹּקֶר וִימֵי הַזְּקֵנָה לָעֶרֶב. וְהַזֶּרַע דֶּרֶךְ מָשָׁל לְבָנִים וְתַלְמִידִים. כְּמוֹ שֶׁאָמְרוּ רַבּוֹתֵינוּ זִכְרוֹנָם לִבְרָכָה נָשָׂא אִשָּׁה בְּיַלְדוּתוֹ יִשָּׂא אִשָּׁה בְּזִקְנוּתוֹ הֶעֱמִיד תַּלְמִידִים בְּיַלְדוּתוֹ יַעֲמִיד תַּלְמִידִים בְּזִקְנוּתוֹ. כִּי אוּלַי יַצְלִיחוּ בְּנֵי הַזְּקוּנִים בַּתּוֹרָה וּבַמִּצְוֹת מִבְּנֵי הַנְּעוּרִים. וְכֵן הַתַּלְמִידִים אֲשֶׁר יַעֲמִיד בְּזִקְנוּתוֹ אוּלַי יַצְלִיחוּ מִן הָרִאשׁוֹנִים אוֹ יִהְיוּ כְּאֶחָד טוֹבִים. אַחֲרֵי כֵן אָמַר (קהלת י"א:ז') וּמָתוֹק הָאוֹר וְטוֹב לַעֵינַיִם לִרְאוֹת אֶת הַשָּׁמֶשׁ. פֵּרוּשׁוֹ – חָזַר לְדַבֵּר עַל יְמֵי הַזִּקְנָה שֶׁהִמְשִׁיל אוֹתָם לָעֶרֶב. וּמִפְּנֵי כִּי הַזָּקֵן לֹא יִטְעַם אֶת אֲשֶׁר יֹאכַל וְאֶת אֲשֶׁר יִשְׁתֶּה כְּדִבְרֵי בַּרְזִלַּי הַגִּלְעָדִי. אָמַר כִּי יֵשׁ לוֹ לַזָּקֵן לֵהָנוֹת בִּמְאוֹר הַשֶּׁמֶשׁ וְאַל תִּקְצַר נַפְשׁוֹ עָלָיו. כִּי קֹצֶר נֶפֶשׁ מוֹנֵעַ אֶת הָאָדָם מִמְּלֶאכֶת שָׁמַיִם. וְיֶעֱרַב לוֹ הָאוֹר כַּאֲשֶׁר יַעַרְכֶנּוּ לְעֻמַּת יְמֵי הַחֹשֶׁךְ הַבָּאִים. כַּאֲשֶׁר יַזְכִּיר בַּמִּקְרָא אֲשֶׁר לְמַטָּה מִזֶּה (קהלת י"א:ח') כִּי אִם שָׁנִים הַרְבֵּה יִחְיֶה הָאָדָם בְּכֻלָּם יִשְׂמָח וְיִזְכֹּר אֶת יְמֵי הַחֹשֶׁךְ כִּי הַרְבֵּה יִהְיוּ כָּל שֶׁבָּא הָבֶל. פֵּרוּשׁ גַּם כִּי יַזְקִין הָאָדָם מְאוֹד אַל יִהְיֶה עַל עַצְמוֹ לְמַשָּׂא. אַךְ בְּכָל שְׁנוֹתָיו יִשְׂמַח לְמַעַן לֹא יְאַבֵּד אַחַת מִשְּׁנוֹתָיו וְלֹא יִשְׁבֹּת מֵעֲבוֹדַת הַבּוֹרֵא. וְיִזְכּוֹר יְמֵי הַחֹשֶׁךְ כִּי הַרְבֵּה יִהְיוּ וְאָז לֹא יוּכַל לַעֲבֹד עֲבוֹדָה כָּעִנְיָן שֶׁנֶּאֱמַר (תהילים ו':ו') בִּשְׁאוֹל מִי יוֹדֶה לָּךְ. וְהַצַּדִּיקִים מִתְגַּבְּרִים בְּזִקְנוּתָם וְיֶאֶזְרוּ חַיִל וְיַחֲלִיפוּ כֹּחַ לַעֲבוֹדַת הַשֵּׁם כְּמוֹ שֶׁאָמְרוּ רַבּוֹתֵינוּ זִכְרוֹנָם לִבְרָכָה תַּלְמִידֵי חֲכָמִים כָּל זְמַן שֶׁמַּזְקִינִין חָכְמָה מִתּוֹסֶפֶת בָּהֶם. וְנֶאֱמַר (תהילים צ"ב:ט"ו) עוֹד יְנוּבוּן בְּשֵׂיבָה דְּשֵׁנִים וְרַעֲנַנִּים יִהְיוּ. וְהִזְכִּיר לְמַעְלָה (תהילים צ"ב:י"ג-י"ד) צַדִּיק כַּתָּמָר יִפְרָח וְגוֹ' שְׁתוּלִים בְּבֵית ה' וְגוֹ' כִּי הַצַּדִּיקִים שְׁתוּלִים בְּבֵית ה' מִנְּעוּרֵיהֶם וּגְדֵלִים בְּבָתֵּי מִדְרָשׁוֹת מִבְּחוּרֵיהֶם. כַּתָּמָר שֶׁיִּפְרַח וְכָאֶרֶז שֶׁגָּדֵל בַּלְּבָנוֹן. וְכֵן אָמְרוּ רַבּוֹתֵינוּ זִכְרוֹנָם לִבְרָכָה שְׁתוּלִים בְּבֵית ה' אֵלּוּ הַתִּינוֹקוֹת עַל דֶּרֶךְ מָה שֶׁכָּתוּב (תהילים קמ"ד:י"ב) אֲשֶׁר בָּנֵינוּ כִּנְטִעִים מְגֻדָּלִים בִּנְעוּרֵיהֶם. וְאָמַר אַחֲרֵי כֵן בְּדָבָר זֶה אֵינָם נִמְשָׁלִים לָאִילָנוֹת כִּי הָאִילָנוֹת בְּהַזְקִינָם לֹא יִתְּנוּ חֵילָם וְהַצַּדִּיקִים יְנוּבוּן בְּשֵׂיבָה. עוֹד אָמַר דָּוִד הַמֶּלֶךְ עָלָיו הַשָּׁלוֹם (תהילים ע"א:י"ח) וְגַם עַד זִקְנָה וְשֵׂיבָה אֱלֹהִים אַל תַּעַזְבֵנִי עַד אַגִּיד זְרוֹעֲךָ לְדוֹר לְכָל יָבֹא גְּבוּרָתֶךָ.

But there are many people for which the light of repentance is obstructed. For since they are innocent and pure in their eyes, they do not avail themselves of the rectification of their actions - as it appears to them that they are [already] rectified, whereas they sin much to God. Is it not written (Ecclesiastes 7:20), "For there is no righteous man on earth who does what is best and doesn’t sin?" But since these people belittle iniquities, they do not feel or understand it; or when they are made known of their sins, it is afterwards forgotten from their hearts. And behold they are like a sick person who does not feel his sickness, so he does not think of a cure. So his sickness constantly gets worse, until he is not able to be healed. And sometimes the reason for this is from their lack of understanding. For they do not go to seek God and do not want to know His ways. Therefore they do not regularly [visit] the doors of the sages and the [Torah] students, like the matter is stated (Proverbs 15:12), "The scoffer dislikes being reproved; he will not resort to the wise." And behold [with] people who are righteous and straight of heart, what constantly roars like a lion in their thoughts and growls like the sea is their sins, and their hands falling short from the service of God. For about [the latter] - when a person transgresses, his guilt grows as with weighty sins, like the matter that our Rabbis, may their memory be blessed, said (Yerushalmi Chagigah 1:7), "The Holy One, blessed be He, forwent about [prohibited] sexual relations, but did not forego about the nullification of Torah (wasting time that should be spent in Torah study). Especially since these people's main thoughts and actions are matters of their body and the vanities of their time, they have done much evil. But to the secret of fear, their souls should not come; and their glory should not be associated with the study of their consciences in the images of their hearts and chambers, and their images for fixed times within which they do not give a portion to Torah [study] among their occupations. And the calculation of their souls has been lost from within their hearts, for they are a nation that loses its counsel. And how much are they on the lowest level! And our Rabbis, may their memory be blessed, said (Avot 5:21), "At sixty, old age; at seventy, fullness of years; at eighty, the age of strength; at ninety, a bent body; at one hundred, as good as dead and gone completely out of the world." And their intention, may their memory be blessed, with these words was to warn about repentance - that when a man reaches the days of old age, he should think about his end, if he did not merit to do so in the days of his youth. And since his time is close to coming, he should leave the matters of his body and his desires and rectify his soul. And when he reaches the days of fullness of years, he should add to the removal of [involvement with] the world from his heart. And according to the reduction of years [left], he should reduce his occupation in the world. And he should constantly seclude himself to meditate about fear of God, to think about his soul, to refine his traits and to seek Torah and [its] commandments. And that which they said, "at ninety, a bent (lasuach) body" is from the [same usage as in] (Psalms 102:1), "spill his prayer (sicho)" [and] (Genesis 24:63), "to pray (lasuach) in the field" - as our Rabbis, may their memory be blessed, said (Berakhot 26b), "Isaac established the afternoon prayers, as it is stated, "to pray (lasuach) in the field." For after one reaches ninety years, it is fitting for him that all of his occupation should be with prayer and praises of God, and to speak about His wonders. And King Solomon, peace be upon him, spoke about the matter of the days of old age - that a person should not then be lazy about service to God, may He be blessed. And he said (Ecclesiastes 11:6), "Sow your seed in the morning, and don’t hold back your hand in the evening, since you don’t know which is going to succeed, the one or the other, or if both are equally good." He compared the days of childhood and youth to the morning and the days of old age to evening. And seed is metaphoric for children and for students, as our Rabbis, may their memory be blessed, said (Yevamot 62b), "If he married a woman in his youth, he should marry [another] one in his old age; if he established students in his youth, he should establish [other] students in his old age." For perhaps the children of old age will be more successful in Torah and in the commandments than the children of youth. And likewise the students that he establishes in his old age may be more successful than the first ones. Or they could both be equally good. Afterwards, he stated (Ecclesiastes 11:7), "How sweet is the light, what a delight for the eyes to behold the sun!" Its explanation is that he went back to speaking about the days of old age which he compared to the evening. And since an old man will not taste that which he eats and that which he drinks - like the words of Barzilai the Gileadite - he stated that the old man should enjoy the light of the sun and not be disgusted by it. As disgust obstructs a person from his service to the Heavens. So he should enjoy the light, when he compares it to the days of darkness that are coming - as it mentions in the verse below this (Ecclesiastes 11:8), "Even if a man lives many years, let him enjoy himself in all of them, remembering how many the days of darkness are going to be; the only future is nothingness!" The explanation is that even if a person get very old, let him not be a burden to himself. Rather he should rejoice in all of his years, so that he not lose one of his years and not rest from the service of the Creator. And he should remember the days of darkness, for they will be many. And then he will not be able to perform the service, like the matter that is stated (Psalms 6:6), "in the pit, who can acclaim You?" And the righteous ones overcome their old age, gird their power and renew their strength for the service of God. It is as our Rabbis, may their memory be blessed, said (Shabbat 152), As Torah scholars grow older, wisdom is increased in them." And it is stated (Psalms 92:15), "In old age they still produce fruit; they are full of sap and freshness." And he mentioned above (Psalms 92:13-14), "The righteous bloom like a date-palm, etc. Planted in the house of the Lord, etc." For the righteous are planted in the house of the Lord from their youth, and grow in the house of study from their young adulthood - like a date-palm that blossoms and like a cedar that grows in the Lebanon. And as our Rabbis, may their memory be blessed, likewise said, (Midrash Tehillim 92:14), "'The righteous bloom like a date-palm' - these are the infants, in the way that it was stated (Psalms 144:12), 'For our sons are like saplings, well-tended in their youth.'" And he stated after this about this thing, that they are not [completely] compared to trees. For trees will not give their strength when they age. But the righteous "in old age, they still produce fruit." And King David, peace be upon him, also stated (Psalms 71:18), "And even in hoary old age do not forsake me, God, until I proclaim Your strength to the next generation, Your mighty acts, to all who are to come."

Why it matters — The authoritative Rishon guide to teshuva preparation for Yom Kippur, detailing each required kavana and inner act.

Source 4 · Rishonim
Verified

Orchot Tzadikim — Gate of Repentance

Orchot Tzadikim 26

The Orchot Tzadikim devotes a full chapter to teshuva, describing the need for genuine remorse, verbal confession with specific mention of each sin, and transformation of character. It also discusses the special power of communal confession and the atonement of Yom Kippur.

תּוֹרָה, תְּשׁוּבָה, גַּן עֵדֶן וְגֵיהִנֹּם, וְכִסֵּא הַכָּבוֹד, וּבֵית הַמִּקְדָּשׁ, וּשְׁמוֹ שֶׁל מָשִׁיחַ. וְלָמָּה אֵלּוּ שִׁבְעָה? דַּע לְךָ, שֶׁעִקַּר בְּרִיאַת הָעוֹלָם הוּא בִּשְׁבִיל הָאָדָם, כִּי אֵין צֹרֶךְ בָּעוֹלָם הַתַּחְתּוֹן אֶלָּא בָּאָדָם, וְהוּא מוֹשֵׁל בְּכָל עוֹלָם הַתַּחְתּוֹן, בִּבְהֵמוֹת וְחַיּוֹת וְעוֹפוֹת וְדָגִים וּשְׁרָצִים. וְכֵיוָן שֶׁהִקְדִּים תּוֹרָה וּתְשׁוּבָה, הֻצְרַךְ לְהַקְדִּים כְּמוֹ כֵן גַּן עֵדֶן וְגֵיהִנָּם וְכִסֵּא הַכָּבוֹד, שֶׁהֵם מְקוֹמוֹת לְשַׁלֵּם לָאִישׁ כְּמַעֲשָׂיו. עֲבוּר שִׁבְעָה דְּבָרִים יַקְדִּים הָאָדָם לָשׁוּב בְּבַחֲרוּתוֹ כְּשֶׁהוּא בְּגֹדֶל כּוֹחוֹ:

The fifth way in which repentance can be aroused is when the Ten Days of Repentance draw near, then every man should arouse his heart and tremble as he goes to meet the Day of Judgment, for he should ponder that all of his deeds are written in a book, and that at this time God will bring to judgment every deed and every hidden thing, whether it be good or bad. For a man is judged on Rosh Hashanah, and his decree is sealed on the Day of Atonement (Rosh Hashana 16a). Therefore, it is proper that everyone who reveres God should lessen his usual occupations and let his thoughts be calm, and let him fix hours, during the day and a night, when he can sit alone in his rooms and examine his ways and search them out, and arise even before the watches of the morning to occupy himself with the paths of repentance. But a man should arouse himself to do complete repentance during the Ten Days of Repentance, for this is a time when God accepts his plea and his prayer is heard, as it is said, "In an acceptable time have I answered thee, and in a day of salvation have I helped thee" (Is. 49:8).

Why it matters — A medieval Mussar text offering detailed practical guidance on the inner work of teshuva and the kavanos of Viduy.

Source 5 · Rishonim
Verified

Chovot HaLevavot — Gate of Repentance

Duties of the Heart, Seventh Treatise on Repentance.3

Rabbeinu Bachya ibn Paquda describes teshuva as fundamentally a movement of the heart (levav), requiring genuine grief over one's sins, recognition of God's greatness and one's own smallness, and a deep inner resolve. He stresses that external acts without inner transformation are worthless.

אֲבָל בַּמֶּה תִּהְיֶה הַתְּשׁוּבָה מֵהָאָדָם אוֹמַר בָּזֶה כִּי תִּתָּכֵן לוֹ אַחַר הַקְדָּמַת יְדִיעָתוֹ בְּשִׁבְעָה דְּבָרִים. 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׳.

- What a man needs to know to repent What are the prerequisites of repentance? I say on this, to be effective, repentance must be preceded by first understanding seven things: (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).

Why it matters — Provides the most thorough medieval account of the inner kavanos — the heart-work — required for genuine Yom Kippur teshuva and prayer.

Source 6 · Acharonim
Verified

Mesillat Yesharim — Chapter on Watchfulness (Zehirut)

Mesillat Yesharim 4

The Ramchal teaches that a person must engage in honest self-accounting (cheshbon hanefesh), carefully examining all of one's deeds and habits. He frames this self-examination as the necessary foundation of all spiritual growth and teshuva.

אָמְנָם עַל דֶּרֶךְ פְּרָט הַמֵּבִיא לָזֶה, הוּא הַהִתְבּוֹנְנוּת עַל חֹמֶר הָעֲבוֹדָה אֲשֶׁר חַיָּב בָּהּ הָאָדָם, וְעֹמֶק הַדִּין עָלֶיהָ. וְיֵצֵא לוֹ זֶה, מִן הָעִיּוּן בַּמַּעֲשִׂים הַכְּתוּבִים בְּסִפְרֵי הַקֹּדֶשׁ וּמִן הַלִּמּוּד בְּמַאַמְרֵי הַחֲכָמִים זִכְרוֹנָם לִבְרָכָה הַמְעוֹרְרִים עַל זֶה.

This realization comes from studying the events reported in the holy books, and from studying the statements of our Sages of blessed memory which rouse one on this. This reflection has varying degrees of arousing, respectively, for those of wholeness of understanding, those of lesser understanding, and for the general masses.

Why it matters — Provides the Mussar framework for spiritual preparation — systematic self-examination — which is the practical method of Yom Kippur readiness.

Source 7 · Acharonim
Verified

Shulchan Arukh — Erev Yom Kippur Laws

Shulchan Arukh, Orach Chayim 606-607

The Shulchan Arukh rules that one must seek forgiveness from anyone one has wronged before Yom Kippur, and that one should confess (viduy) on Erev Yom Kippur before the meal. It also discusses the minhag of immersion in a mikveh as a preparatory act of purity.

שיפייס אדם חבירו בערב יום כפור. ובו ד סעיפים: עבירות שבין אדם לחבירו אין יום הכפורים מכפר עד שיפייסנו ואפילו לא הקניטו אלא בדברים צריך לפייסו ואם אינו מתפייס בראשונה יחזור וילך פעם שניה ושלישית ובכל פעם יקח עמו שלשה אנשים ואם אינו מתפייס בשלשה פעמים אינו זקוק לו (מיהו יאמר אח"כ לפני עשרה שביקש ממנו מחילה). (מרדכי דיומא ומהרי"ל) ואם הוא רבו צריך לילך לו כמה פעמים עד שיתפייס: הגה והמוחל לא יהיה אכזרי מלמחול (מהרי"ל) אם לא שמכוין לטובת המבקש מחילה (גמרא דיומא) ואם הוציא עליו שם רע א"צ למחול לו (מרדכי וסמ"ק והגה"מ פ"ב מהלכות תשובה ומהרי"ו): סדר הוידוי במנחה בערב יום כפור. ובו ו סעיפים: צריך להתודות במנחה קודם סעודה המפסקת: הגה ויחיד אומרו אחר שגמר תפלתו וש"ץ אומרו ביו"כ בתוך התפלה (טור): צריך להתודות מעומד ואפילו כי שמע ליה משליח צבור והוא התודה כבר צריך לעמוד: הגה ויחזור ויתודה עם השליח צבור (ר"ן פ"ב דר"ה) ועיקר הוידוי היא אבל אנחנו חטאנו (טור):

“A man should appease his friend (i.e., a person whom he wronged) on the Eve of Yom Kippur” - Containing four paragraphs. Yom Kippur does not atone for sins between a man and his comrad (fellow-man) until he conciliates him. Even if he angered him only in words, he is required to appease him (his fellow-man). And if at first he is not pacified, he (must) return and go to him a second and third time. Each time he should take three men with him, and if on the third time he does not become reconciled he (no longer) is obligated to him, (nevertheless afterwards he should say before ten (people) that he did request forgiveness from him), (מרדכי דיומא ומהרי״ל). If he (i.e., the person who was wronged) was his teacher, he must go to him many times until he becomes appeased. Hagah: The person to forgive should not be cruel by refusing forgiveness (to the one seeking forgiveness), (מהרי״ל), unless his intent is for the good of the one requesting forgiveness, (גמרא דיומא). But if one caused him (the wronged person) a bad name, there is no necessity in forgiving him, (מרדכי וסמ״ק והגה״מ פ״ב מהלכות תשובה ומהרי״ו). “The order of confession (of sins) during Minḥah (the Afternoon Prayer) on the Eve of Yom Kippur” - Containing six paragraphs. One needs to confess during Minḥah (the Afternoon Prayer) before the (last) meal before fasting. Hagah: If one is alone he says it (the confessional) after he finished his Silent Prayer, but the public reader says his (confessional) on Yom Kippur during the Silent Prayer, (טור). One has to confess standing up and even if one (the confessor) hears it from the reader and he has already confessed, he still must stand. Hagah: And one should again confess with the reader, (ר״ן פ״ב דר״ה); the essence of the confession is “but we sinned”, (טור).

Why it matters — The authoritative halakhic code detailing the specific preparatory acts — seeking forgiveness, mikveh, and viduy — required before Yom Kippur.