Rabbeinu Yonah opens his classic work on repentance by enumerating twenty foundational principles of teshuva, including regret, shame, abandonment of sin, prayer, restitution, and pursuing the path of virtue. He emphasizes that the severity of the sin determines the depth of repentance required.
הַשַּׁעַר הָרִאשׁוֹן – בְּבֵאוּר הַתְּשׁוּבָה וְעִקָּרֶיהָ. מִן הַטּוֹבוֹת אֲשֶׁר הֵיטִיב הַשֵּׁם יִתְבָּרַךְ עִם בְּרוּאָיו, כִּי הֵכִין לָהֶם הַדֶּרֶךְ לַעֲלוֹת מִתּוֹךְ פַּחַת מַעֲשֵׂיהֶם וְלָנוּס מִפַּח פִּשְׁעֵיהֶם, לַחְשֹׂךְ נַפְשָׁם מִנִּי שַׁחַת וּלְהָשִׁיב מֵעֲלֵיהֶם אַפּוֹ, וְלִמְּדָם וְהִזְהִירָם לָשׁוּב אֵלָיו כִּי יֶחֶטְאוּ לוֹ, לְרֹב טוּבוֹ וְיָשְׁרוֹ כִּי הוּא יָדַע יִצְרָם, שֶׁנֶּאֱמַר (תהלים כה, ח): "טוֹב וְיָשָׁר ה' עַל כֵּן יוֹרֶה חַטָּאִים בַּדָּרֶךְ", וְאִם הִרְבּוּ לִפְשֹׁעַ וְלִמְרוֹד וּבֶגֶד בּוֹגְדִים בָּגָדוּ, לֹא סָגַר בַּעֲדָם דַּלְתֵי תְּשׁוּבָה, שֶׁנֶּאֱמַר (ישעיה לא, ו): "שׁוּבוּ לַאֲשֶׁר הֶעְמִיקוּ סָרָה". וְנֶאֱמַר (ירמיה ג, כב): "שׁוּבוּ בָּנִים שׁוֹבָבִים אֶרְפָּה מְשׁוּבֹתֵיכֶם". וְהֻזְהַרְנוּ עַל הַתְּשׁוּבָה בְּכַמָּה מְקוֹמוֹת בַּתּוֹרָה, וְהִתְבָּאֵר, כִּי הַתְּשׁוּבָה מְקֻבֶּלֶת גַּם כִּי יָשׁוּב הַחוֹטֵא מֵרֹב צָרוֹתָיו, כָּל שֶׁכֵּן אִם יָשׁוּב מִיִּרְאַת הַשֵּׁם וְאַהֲבָתוֹ, שֶׁנֶּאֱמַר (דברים ד, ל): "בַּצַּר לְךָ וּמְצָאוּךָ כֹּל הַדְּבָרִים הָאֵלֶּה בְּאַחֲרִית הַיָּמִים וְשַׁבְתָּ עַד ה' אֱלֹהֶיךָ וְשָׁמַעְתָּ בְּקוֹלוֹ". וְהִתְבָּאֵר בַּתּוֹרָה, כִּי יַעֲזֹר ה' לַשָּׁבִים כַּאֲשֶׁר אֵין יַד טִבְעָם מַשֶּׂגֶת וִיחַדֵּשׁ בְּקִרְבָּם רוּחַ טְהוֹרָה לְהַשִּׂיג מַעֲלַת אַהֲבָתוֹ, שֶׁנֶּאֱמַר (דברים ל, ב): "וְשַׁבְתָּ עַד ה' אֱלֹהֶיךָ וְשָׁמַעְתָּ בְקֹלוֹ כְּכֹל אֲשֶׁר אָנֹכִי מְצַוְּךָ הַיּוֹם אַתָּה וּבָנֶיךָ בְּכָל לְבָבְךָ וּבְכָל נַפְשֶׁךָ". וְאוֹמֵר בְּסוֹף הָעִנְיָן (דברים ל, ו): "וּמָל ה' אֱלֹהֶיךָ אֶת לְבָבְךָ וְאֶת לְבַב זַרְעֶךָ" – לְהַשִּׂיג אַהֲבָתוֹ. וְהַנְּבִיאִים וְהַכְּתוּבִים דִּבְּרוּ תָּמִיד עַל דְּבַר הַתְּשׁוּבָה, עַד כִּי בָּאוּ עִקְּרֵי הַתְּשׁוּבָה כֻּלָּם מְפֹרָשִׁים בְּדִבְרֵיהֶם כַּאֲשֶׁר יִתְבָּאֵר. הָעִקָּר הָרִאשׁוֹן – הַחֲרָטָה: יָבִין לְבָבוֹ כִּי רַע וָמָר עָזְבוֹ אֶת ה', וְיָשִׁיב אֶל לִבּוֹ כִּי יֵשׁ עֹנֶשׁ וְנָקָם וְשִׁלֵּם עַל הֶעָוֹן, כָּעִנְיָן שֶׁנֶּאֱמַר (דברים לב, לה): "לִי נָקָם וְשִׁלֵּם", וְנֶאֱמַר (איוב יט, כט): "גּוּרוּ לָכֶם מִפְּנֵי חֶרֶב כִּי חֵמָה עֲוֹנוֹת חָרֶב". וְיִתְחָרֵט עַל מַעֲשָׂיו הָרָעִים, וְיֹאמַר בִּלְבָבוֹ: מֶה עָשִׂיתִי? אֵיךְ לֹא הָיָה פַּחַד אֱלֹקִים לְנֶגֶד עֵינַי, וְלֹא יָגֹרְתִּי מִתּוֹכָחוֹת עַל עָוֹן וּמִן הַשְּׁפָטִים הָרָעִים, כִּי רַבִּים מַכְאוֹבִים לָרָשָׁע? לֹא חָמַלְתִּי עַל גּוּפִי, וְלֹא חָסָה עֵינִי עָלָיו מִשַּׁחֲתוֹ מִפְּנֵי הֲנָאַת רֶגַע אֶחָד, וְנִמְשַׁלְתִּי לְאִישׁ שֶׁיִּגְזֹל וְיַחְמֹס וְיֹאכַל וְיִשְׂבַּע, וְיוֹדֵעַ כִּי אַחֲרֵי אָכְלוֹ וְאַחֲרֵי שָׁתוֹ יַגְרֵס הַשּׁוֹפֵט בֶּחָצָץ שִׁנָּיו, כָּעִנְיָן שֶׁנֶּאֱמַר (משלי כ, יז): "עָרֵב לָאִישׁ לֶחֶם שָׁקֶר וְאַחַר יִמָּלֵא פִיהוּ חָצָץ". וְרָעָה מִזֹּאת, כִּי הָיִיתִי עַל הַנֶּפֶשׁ הַיְּקָרָה אַכְזָרִי וְנִטְמְאָה בְּגִלּוּלֵי יִצְרִי, וּמָה הוֹעִילָה בְּכָל קִנְיָנֶיהָ אִם רָעָה בְּעֵינֵי אֲדֹנֶיהָ? וְאֵיךְ הֶחֱלַפְתִּי בְּעוֹלָם חוֹלֵף, עוֹלָם עוֹמֵד לָעַד לְעוֹלָם? אֵיךְ נִמְשַׁלְתִּי כִּבְהֵמוֹת נִדְמֵיתִי, וְהָלַכְתִּי אַחֲרֵי יִצְרִי כְּסוּס כְּפֶרֶד אֵין הָבִין וְתָעִיתִי מִדֶּרֶךְ הַשְׁכֵּל? וְהִנֵּה הַבּוֹרֵא נָפַח בְּאַפִּי נִשְׁמַת חַיִּים חַכְמַת לֵב וְטוֹבַת שֵׂכֶל לְהַכִּירוֹ וּלְיִרְאָה מִלְּפָנָיו וְלִמְשׁוֹל בַּגּוּף וְכָל תּוֹלְדוֹתָיו כַּאֲשֶׁר הִמְשִׁילָהּ עַל שְׁאָר בַּעֲלֵי חַיִּים שֶׁאֵינָם מְדַבְּרִים מֵאֲשֶׁר יָקְרָה בְּעֵינָיו נִכְבְּדָה, וְאַחֲרֵי אֲשֶׁר בַּעֲבוּר זֹאת נִבְרֵאתִי, וַיְהִי בִּי הֵפֶךְ מִזֶּה, לָמָּה לִי חַיִּים? כָּעִנְיָן שֶׁנֶּאֱמַר (משלי כא, טז): "אָדָם תּוֹעֶה מִדֶּרֶךְ הַשְׂכֵּל בִּקְהַל רְפָאִים יָנוּחַ". וְעוֹד, כִּי כְּמִשְׁפַּט הַבְּהֵמָה לֹא עָשִׂיתִי, אֲבָל שָׁפַלְתִּי מִמֶּנָּה, כִּי יָדַע שׁוֹר קֹנֵהוּ וַחֲמוֹר אֵבוּס בְּעָלָיו, וַאֲנִי לֹא יָדַעְתִּי וְלֹא הִתְבּוֹנַנְתִּי, וְשָׁלַחְתִּי נַפְשִׁי לַחָפְשִׁי מֵאֲדוֹנֶיהָ, וְטָעַמְתִּי צוּפִי, וְנָשִׁיתִי סוֹפִי, וְגָזַלְתִּי וְחָמַסְתִּי, וְעַל דָּל בּוֹסַסְתִּי, וְלֹא זָכַרְתִּי יוֹם הַמָּוֶת אֲשֶׁר לֹא יַשְׁאִיר לִפְנֵי נִשְׁמָתִי בִּלְתִּי אִם גְּוִיָּתִי וְאַדְמָתִי. וְהָעִנְיָן הַזֶּה אֲשֶׁר בֵּאַרְנוּ הוּא אֲשֶׁר דִּבֶּר יִרְמְיָה עָלָיו הַשָּׁלוֹם (ירמיה ח, ו): "אֵין אִישׁ נִחָם עַל רָעָתוֹ לֵאמֹר מֶה עָשִׂיתִי". הָעִקָּר הַשֵּׁנִי – עֲזִיבַת הַחֵטְא: כִּי יַעֲזֹב דְּרָכָיו הָרָעִים וְיִגְמֹר בְּכָל לְבָבוֹ כִּי לֹא יוֹסִיף לָשׁוּב בַּדֶּרֶךְ הַזֶּה עוֹד, וְאִם אָוֶן פָּעַל לֹא יוֹסִיף, כָּעִנְיָן שֶׁנֶּאֱמַר (יחזקאל לג, יא): "שׁוּבוּ שׁוּבוּ מִדַּרְכֵיכֶם הָרָעִים", וְנֶאֱמַר (ישעיה נה, ז): "יַעֲזֹב רָשָׁע דַּרְכּוֹ". וְדַע, כִּי מִי אֲשֶׁר חָטָא עַל דֶּרֶךְ מִקְרֶה, כִּי הִתְאַוָּה תַּאֲוָה וַיֶּחֱזַק עָלָיו יִצְרוֹ וַיִּתְקְפֵהוּ, וְלֹא נֶחְלְצוּ רַעְיוֹנָיו וְחוּשָׁיו בְּפָגְעוֹ בּוֹ, וְלֹא מִהֲרוּ לִגְעֹר בְּיַם הַתַּאֲוָה וְיֶחְרַב, עַל כֵּן יְגֹרֵהוּ הַיֵּצֶר בַּחֲרָמָיו, וְנָפַל בְּמַכְמוֹרָיו לְפִי שְׁעָתוֹ וְעִתּוֹ, בִּהְיוֹת רוּחַ הַיֵּצֶר רַע מְבַעֲתוֹ, וְלֹא מֵאֲשֶׁר חֶפְצוֹ וּרְצוֹנוֹ לִמְצוֹא עֲוֹנוֹ, וְלַעֲשׂוֹת כָּמוֹהוּ אַחֲרֵי זֹאת – רֵאשִׁית תְּשׁוּבַת הָאִישׁ הַזֶּה הַחֲרָטָה, וְלָשִׂים יָגוֹן בְּלִבּוֹ עַל חַטָּאתוֹ וְלִהְיוֹת נֶפֶשׁ נַעֲנָה וּמָרָה כַּלַּעֲנָה, אַחֲרֵי כֵן יוֹסִיף בְּכָל יוֹם יִרְאַת ה' בְּנַפְשׁוֹ, וְיִתֵּן חִתַּת אֱלֹקִים בִּלְבָבוֹ בְּכָל עֵת, עַד אֲשֶׁר יִהְיֶה נָכוֹן לִבּוֹ בָּטֻחַ בַּה', כִּי אִם יוֹסִיף יַעֲבֹר בּוֹ הַיֵּצֶר וַיִּפְגְּשֵׁהוּ כְּפַעַם בְּפַעַם, וְרַבָּה עָלָיו תַּאֲוָתוֹ כַּמִּשְׁפָּט הָרִאשׁוֹן. לֹא יִהְיֶה נִפְתֶּה לִבּוֹ עָלָיו – וְיַעֲזֹב דַּרְכּוֹ, כְּמוֹ שֶׁנֶּאֱמַר (משלי כח, יג): "וּמוֹדֶה וְעוֹזֵב יְרֻחָם", הִזְכִּיר תְּחִלָּה "וּמוֹדֶה" עַל הַחֲרָטָה וְהַוִּדּוּי, וְאַחַר כָּךְ "וְעוֹזֵב". אַךְ הָאִישׁ הַמִּתְיַצֵּב עַל דֶּרֶךְ לֹא טוֹבָה תָּמִיד, וְגֶבֶר עַל חֲטָאָיו דּוֹרֵךְ בְּכָל יוֹם, וְשׁוֹנֶה בְּאִוַּלְתּוֹ וְשָׁב בִּמְרוּצָתוֹ גַּם פְּעָמִים רַבּוֹת, וְכָל עֵת אוֹהֵב הָרֵעַ, וּמִכְשׁוֹל עֲוֹנוֹ יָשִׂים נֹכַח פָּנָיו, רוֹצֶה לוֹמַר הַתַּאֲוָה וְהַיֵּצֶר, וְחֶפְצוֹ וּמְגַמָּתוֹ, אֲשֶׁר לֹא יִבָּצֵר מִמֶּנּוּ כָּל אֲשֶׁר יָזַם לַעֲשׂוֹת – רֵאשִׁית תְּשׁוּבַת הָאִישׁ הַזֶּה, לַעֲזֹב דַּרְכּוֹ וּמַחֲשַׁבְתּוֹ הָרָעָה, וּלְהַסְכִּים לְקַיֵּם וּלְקַבֵּל עָלָיו לְבַל יוֹסִיף לַחֲטוֹא, אַחֲרֵי כֵן יִתְחָרֵט עַל עֲלִילוֹתָיו הַנִּשְׁחָתוֹת, וְיִתְוַדֶּה לָשׁוּב אֶל ה', כְּמוֹ שֶׁנֶּאֱמַר (ישעיה נה, ז): "יַעֲזֹב רָשָׁע דַּרְכּוֹ וְאִישׁ אָוֶן מַחְשְׁבֹתָיו וְיָשֹׁב אֶל ה' וִירַחֲמֵהוּ". וְהַמָּשָׁל בָּזֶה – לְמִי שֶׁאוֹחֵז הַשֶּׁרֶץ וּבָא לִטְבֹּל וּלְהִטָּהֵר, כִּי יַנִּיחַ הַשֶּׁרֶץ תְּחִלָּה וְאַחֲרֵי כֵן יִטְבֹּל וְיִטְהַר. וְכָל זְמַן שֶׁהַשֶּׁרֶץ בְּיָדוֹ – עוֹד טֻמְאָתוֹ בּוֹ וְאֵין הַטְּבִילָה מוֹעִילָה. וְהִנֵּה עֲזִיבַת מַחְשֶׁבֶת הַחֵטְא – הִיא הַשְׁלָכַת הַשֶּׁרֶץ, וְהַחֲרָטָה מֵאֲשֶׁר חָטָא וְהַוִּדּוּי וְהַתְּפִלָּה – בִּמְקוֹם הַטְּבִילָה. וְהָיָה כִּי יָבוֹאוּ יִסּוּרִים וּמַכְאוֹבִים עַל הָרָשָׁע אֲשֶׁר תָּמִיד כָּל זְמָמָיו לְהִתְהַלֵּךְ בַּאֲשָׁמָיו, יִוָּסֵר בַּתְּחִלָּה וְיָשׁוּב מַחֲשַׁבְתּוֹ הָרָעָה אֲשֶׁר חָשַׁב וְיַכְרִית מַעְבָּדָיו מִיָּדָיו. וְהַמָּשָׁל בָּזֶה – לְעֵגֶל אֲשֶׁר יַכּוּהוּ בְּמַלְמַד הַבָּקָר לְכַוֵּן תְּלָמָיו; כֵּן הַמִּתְיַצֵּב עַל דֶּרֶךְ לֹא טוֹבָה, יִקַּח הַמּוּסָר תְּחִלָּה לַעֲזֹב דַּרְכֵי מָוֶת לָלֶכֶת דֶּרֶךְ יָשָׁר, כְּמוֹ שֶׁנֶּאֱמַר (ירמיה לא, יח): "שָׁמוֹעַ שָׁמַעְתִּי אֶפְרַיִם מִתְנוֹדֵד יִסַּרְתַּנִי וָאִוָּסֵר כְּעֵגֶל לֹא לֻמָּד". עוֹד נֶאֱמַר אַחֲרָיו (ירמיה לא, יט): "כִּי אַחֲרֵי שׁוּבִי נִחַמְתִּי", רוֹצֶה לוֹמַר, כִּי אַחֲרֵי אֲשֶׁר יִסַּרְתַּנִי וְאִוָּסֵר וְשַׁבְתִּי מִדַּרְכִּי הָרָעָה – נִחַמְתִּי אַחֲרֵי כֵן וָאֶתְחָרֵט עַל מָה שֶׁעָבַר מִדִּבְרֵי עֲוֹנֹתַי. וְהִנֵּה נִתְבָּאֵר לְךָ מִזֶּה כָּל הָעִנְיָן אֲשֶׁר בֵּאַרְנוּ.
In explanation of repentance and its principles Among the good things which God, may He be blessed, has bestowed upon His creations is the path which He prepared for them to ascend from the baseness of their actions, to escape the trap of their inequities, to hold their souls back from destruction and to remove His anger from upon them. Because of His goodness and uprightness, He has taught them and warned them to return to Him when they sin against Him - for He understands their nature, as it is stated (Psalms 25:8), "Good and upright is the Lord; therefore He shows sinners the way." [Even] if they greatly sin and rebel and act like treacherous betrayers - He does not close the doors of repentance to them, as it is stated (Isaiah 31:6), "Return, to Him to whom they have been so shamefully false." It is [also] stated (Jeremiah 3:22), "Turn back, O rebellious children, I will heal your afflictions." We are warned about repentance in several places in the Torah. It is explained that repentance is accepted even when the sinner repents because of his many troubles - how much more so [will it be accepted] if he returns because of fear or love of God - as it is stated (Deuteronomy 4:30), "When you are in distress because all these things have befallen you and, in the end, return to the Lord your God and obey Him." It is explained in the Torah that God will help those who repent beyond what their natural ability would allow; and that He renews a pure spirit within them, to reach great heights in His love - as it is stated (Deuteronomy 30:2), "And you return to the Lord your God, and you and your children heed His command with all your heart and soul, just as I enjoin upon you this day." Further, it is stated about the body of the matter (Deuteronomy 30:6), "Then the Lord, your God, will circumcise your heart and the hearts of your offspring," to acquire love for Him. And the Prophets and Writings constantly speak on the subject of repentance, such that the principles of repentance are all explained in their words, as will be explained. Now we will explain the principles of repentance. The first principle is regret: His heart should understand that leaving God is bad and bitter; and he should place into his heart that there is punishment, vengeance and repayment for iniquity, as it is stated (Deuteronomy 32:35), "To be My vengeance and repayment." And it is stated (Job 19:29), "Be in fear of the sword, for [your] fury is iniquity worthy of the sword." And he should regret his bad deeds and say in his heart, "What have I done? How did I not have fear of God in front of my eyes, and did not become afraid from the rebukes of iniquity and from the harsh judgments? For there are many aches [waiting] for the evildoer. I did not pity my body; and for a moment of pleasure, my eyes did not pity its being destroyed. I became like a man who robs and extorts, eats and is satiated; but who knows that after his eating and his drinking, the judge will grind his teeth with gravel - like the matter that is stated (Proverbs 20:17), 'but later his mouth will be filled with gravel.' And worse than this, I was cruel to the dear soul and I rendered it impure with the idols of my impulse. And what did it gain from all of its acquisitions, if they are bad in the eyes of its Master? And how did I trade a passing world for a world that exists for ever and ever? How have I become similar to animals? As I have gone after my impulse like a horse, like a mule that does not understand. And I have strayed from the way of the intellect. And behold the Creator blew a living soul into my nose - a wise heart and the benefit of intellect - in order to recognize Him and fear Him and to govern over the body and all of its actions, like it governs over the other animals that do not speak, because it is precious in His eyes. And though I was created like this, it has become the opposite of this in me. Why am I alive? It is like the matter that is stated (Proverbs 21:16), 'A man who strays from the path of the intellect will rest in the company of ghosts.' Moreover I have not [even] fulfilled the precept of the animal. Rather I have been lower than that. For the ox knows its master and the donkey the trough of its owner; whereas I have not known and not reflected. And I have sent my soul to be free from its master. So I have tasted my nectar, but forgotten my end. And I have stolen and extorted and trampled upon the indigent. I have not remembered the day of death, upon which nothing will remain before my soul besides my corpse and my dirt." And this matter that we have explained is that which Jeremiah, peace be upon him, had spoken, "No one regrets his wickedness and says, 'What have I done?'" The second principle is leaving the sin: That he should leave his evil ways and decide with all of his heart that he will not continue to return this way again. And if he did evil, he shall not do [it any] more, like the matter that is stated, (Ezekiel 33:11), "Return, return from your evil ways"; and [likewise] stated (Isaiah 55:17), "Let the wicked give up his ways." But know that [in the case of] one who sins by happenstance because he had a desire and his impulse overpowered him and attacked him, whereas his ideas and senses did not rescue him when he encountered it; so they were not quick to rebuke him in the sea of desire, to dry it up - hence the impulse dragged him into its nets and he fell into its snares at that particular time and instant, at the time that the spirit of the evil impulse kicked him down, but not because of his [own] desire and will to find his iniquity and to do like this afterwards: The beginning of the repentance of this man is regret; to place sorrow into his heart about his sin, to have his soul be afflicted and bitter like wormwood. Afterwards, he should increase the fear of sin in his heart every day, and put the dread of God into his heart at all times, until his heart becomes steady in the trust of God. As if the impulse comes across him again - like it does from time to time - and his desire become fanned like the first case, his heart will not be seduced by it and he will abandon its path. [This is] as it is stated (Proverbs 28:13), "but one who confesses and abandons [them] will find mercy" - it mentions "confesses" first, about the regret and the confession; and afterwards, "abandons." However [in the case of] one who is constantly positioned on the path that is not good, and the man who treads on his sins every day and repeats them in his foolishness; and who runs after it many times in his race, loves his evil all the time, places the trap of his iniquity in front of his face - meaning his desire and impulse - and his craving is his occupation; he does not prevent himself from doing anything that he wants to do: For such a man, the beginning of his repentance is to abandon his evil way and thoughts, and to agree, resolve and accept upon himself to not continue sinning. Afterwards, he should regret and return to God, as it is stated (Isaiah 55:7), "Let the wicked give up his ways, the sinful man his plans; let him turn back to the Lord, and He will pardon him." And the parable for this is about one who holds a sherets (an impure crawling animal) and comes to immerse and become pure. For he must first leave the sherets, and then immerse and become purified. But all the time that the sherets is in his hand, his impurity is still with him and the immersion is ineffective. And behold that leaving the thoughts of sin is [equivalent to] throwing out the sherets; and the regret of that which he sinned, the confession and the prayer are in place of the immersion. And when afflictions and aches come upon the evildoer for whom all of his plans are to continue with his crimes, he is first afflicted. And then he repents from the evil thoughts that he thought and cuts off the actions from his hands. And the parable for this is about a calf which they hit with a cow prod to direct his [work on the] furrows. So is one who is positioned on a path that is not good. He should take the chastisement first, to abandon the ways of death and to walk in a straight path - as it is written (Jeremiah 31:18), "I can hear Ephraim lamenting, 'You have chastised me, and I am chastised like a calf that has not been broken.'" And it is further stated after it (Jeremiah 31:19), "Now that I have turned back, I am filled with remorse." [This] means to say, "After you chastised me, and I was chastised and returned from my evil ways; I was filled with remorse afterwards and regretted what occurred with my iniquities." So behold that all of this matter that we have explained has been clarified for you.