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The Oys and Joys of Parenting: Ethical Jewish Parenting
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(ו) וְהָי֞וּ הַדְּבָרִ֣ים הָאֵ֗לֶּה אֲשֶׁ֨ר אָנֹכִ֧י מְצַוְּךָ֛ הַיּ֖וֹם עַל־לְבָבֶֽךָ׃ (ז) וְשִׁנַּנְתָּ֣ם לְבָנֶ֔יךָ וְדִבַּרְתָּ֖ בָּ֑ם בְּשִׁבְתְּךָ֤ בְּבֵיתֶ֙ךָ֙ וּבְלֶכְתְּךָ֣ בַדֶּ֔רֶךְ וּֽבְשָׁכְבְּךָ֖ וּבְקוּמֶֽךָ׃

(6) Take to heart these things which I command you this day. (7) And you shall teach them to your children, and speak of them when you sit at home and when you walk upon your path, and when you lie down and when you get up.

The word v'shinnantam, "teach," literally means "to repeat over and over." What does this mean about a parent's obligation to their child?
What?

תְּנֵינָא לְהָא דְּתָנוּ רַבָּנַן הָאָב חַיָּיב בִּבְנוֹ לְמוּלוֹ וְלִפְדוֹתוֹ וּלְלַמְּדוֹ תּוֹרָה וּלְהַשִּׂיאוֹ אִשָּׁה וּלְלַמְּדוֹ אוּמָּנוּת וְיֵשׁ אוֹמְרִים אַף לַהֲשִׁיטוֹ בַּמַּיִם

The Gemara comments: According to this interpretation, we learn in this mishna that which the Sages taught in a baraita: A father is obligated with regard to his son to circumcise him, and to redeem him if he is a firstborn son who must be redeemed by payment to a priest, and to teach him Torah, and to marry him to a woman, and to teach him a trade. And some say: A father is also obligated to teach his son to swim.

The story goes that The Baal Shem Tov brought coffee to Rabbi Yitzchak and served it to him. After he drank it, the Baal Shem Tov removed the coffeepot, the cup, and the spoon and brought it to the kitchen. Rabbi Yitzchak's son observed this and asked the Baal Shem Tov: "Holy Rabbi, why did you trouble yourself to carry out the empty dishes?" The Baal Shem Tov answered by explaining that carrying the spoon out from the Holy of Holies (the Temple) was part of the service of the high priest on Yom Kippur. then and now, clearing the table can be an act of great devotion to God.
When?
הוּא הָיָה אוֹמֵר, בֶּן חָמֵשׁ שָׁנִים לַמִּקְרָא, בֶּן עֶשֶׂר לַמִּשְׁנָה, בֶּן שְׁלשׁ עֶשְׂרֵה לַמִּצְוֹת, בֶּן חֲמֵשׁ עֶשְׂרֵה לַתַּלְמוּד, בֶּן שְׁמֹנֶה עֶשְׂרֵה לַחֻפָּה, בֶּן עֶשְׂרִים לִרְדֹּף, בֶּן שְׁלשִׁים לַכֹּחַ, בֶּן אַרְבָּעִים לַבִּינָה, בֶּן חֲמִשִּׁים לָעֵצָה, בֶּן שִׁשִּׁים לַזִּקְנָה, בֶּן שִׁבְעִים לַשֵּׂיבָה, בֶּן שְׁמֹנִים לַגְּבוּרָה, בֶּן תִּשְׁעִים לָשׁוּחַ, בֶּן מֵאָה כְּאִלּוּ מֵת וְעָבַר וּבָטֵל מִן הָעוֹלָם:
He used to say: At five years of age the study of Scripture; At ten the study of Mishnah; At thirteen subject to the commandments; At fifteen the study of Talmud; At eighteen the bridal canopy; At twenty for pursuit [of livelihood]; At thirty the peak of strength; At forty wisdom; At fifty able to give counsel; 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.
Who?
Mishneh Torah, Torah Study 5:12-13
Even as the students are obliged to honor the master, so is the master obliged to treat his disciples with deference and to draw them near himself. Thus said the sages: "Ever let the honor of thy disciple be dear unto thee even as thine own." (Pirke Abot, 4.15). And it is essential for a man to care for his disciples and to love them, for they are the sons who make life enjoyable, both, in this world and in the world to come. The students increase the master's wisdom and broaden his heart. The sages said: "Much wisdom have I learned from my masters, more than that from my colleagues…

אָמַר רַבִּי יְהוֹשֻׁעַ בֶּן לֵוִי כׇּל הַמְלַמֵּד אֶת בֶּן בְּנוֹ תּוֹרָה מַעֲלֶה עָלָיו הַכָּתוּב כְּאִילּוּ קִבְּלָהּ מֵהַר סִינַי

Rabbi Yehoshua ben Levi says: Anyone who teaches his son’s son Torah, the verse ascribes him credit as though he received it from Mount Sinai.

How?
חוֹשֵׂ֣ךְ שִׁ֭בְטוֹ שׂוֹנֵ֣א בְנ֑וֹ וְ֝אֹהֲב֗וֹ שִׁחֲר֥וֹ מוּסָֽר׃
He who spares the rod hates his son,
But he who loves him disciplines him early.
וְאֵלֶּה שְׁמוֹת, זֶה שֶׁאָמַר הַכָּתוּב: חוֹשֵׂךְ שִׁבְטוֹ שׂוֹנֵא בְנוֹ וְאֹהֲבוֹ שִׁחֲרוֹ מוּסָר (משלי יג, כד). בְּנֹהַג שֶׁבָּעוֹלָם, אָדָם שֶׁאָמַר לַחֲבֵרוֹ, פְּלוֹנִי הִכָּה אֶת בִּנְךָ, יוֹרֵד עִמּוֹ עַד לְחַיָּיו. וּמַה תַּלְמוּד לוֹמַר: חוֹשֵׂךְ שִׁבְטוֹ שׂוֹנֵא בְנוֹ? לְלַמֶּדְךָ, שֶׁכָּל הַמּוֹנֵעַ בְּנוֹ מִן הַמַּרְדּוּת, סוֹף יוֹצֵא לְתַרְבּוּת רָעָה וְשׂוֹנְאֵהוּ. שֶׁכֵּן מָצִינוּ בְּיִשְׁמָעֵאל שֶׁהָיָה לוֹ גַּעְגּוּעִין עַל אַבְרָהָם אָבִיו וְלֹא רִדָּהוּ, וְיָצָא לְתַרְבּוּת רָעָה, וּשְׂנָאוֹ אַבְרָהָם וְהוֹצִיאוֹ מִבֵּיתוֹ רֵיקָם.

Scripture states: One who spares the rod hates their child. . . (Prov. 13:24). This teaches you that whenever a person fails to chastise their children, they will ultimately act wickedly, and [the parent] will come to despise them. We find this to be so in the case of Ishmael, who behaved fondly toward his father, who failed to chastise him, and he thus went astray. As a result, Abraham began to despise him, and drove him empty-handed from his home.

Pele Yoetz 3:1
The love of sons and daughters is necessitated by nature, for they are the bone from our bone and flesh of our flesh. But one must take care that this love does not overturn boundaries, that [the parent(s)] do not make their child suffer. Solomon has already said in his wisdom (Proverbs 13:24): One who spares the rod hates their child; those who love their children discipline them early. Therefore, parents should be careful to behave toward their children with open rebuke and hidden love. . . But the parent should take care not to be cruel to their child and not to hit them and give them a bruise out of anger. Rather they should lead with gentleness and mercy,
חֲנֹ֣ךְ לַ֭נַּעַר עַל־פִּ֣י דַרְכּ֑וֹ גַּ֥ם כִּי־יַ֝זְקִ֗ין לֹֽא־יָס֥וּר מִמֶּֽנָּה׃
Train a lad in the way he ought to go;
He will not swerve from it even in old age.
Wendy Mogel from the book The Blessing of a Skinned Knee:
Children “will only accept your guidance and heed your advice if they respect you. ... If you don’t teach your children to honor you, you’ll have a very hard time teaching them anything else.” By honoring their parents, children will be more likely to respect authority, the older generation, and in turn, make the leap from family to community. Their reward will thus be length in days to contribute to this world.
Mishnah Yoma 82a:1
With regard to the children, one does not afflict them by withholding food on Yom Kippur; however, one trains them one year before or two years before they reach majority, by means of a partial fast lasting several hours, so that they will be accustomed to fulfill mitzvot.
רַבִּי אֶלְעָזָר בֶּן שַׁמּוּעַ אוֹמֵר, יְהִי כְבוֹד תַּלְמִידְךָ חָבִיב עָלֶיךָ כְּשֶׁלְּךָ, וּכְבוֹד חֲבֵרְךָ כְּמוֹרָא רַבְּךָ, וּמוֹרָא רַבְּךָ כְּמוֹרָא שָׁמָיִם:
Rabbi Elazar ben Shammua said: let the honor of your student be as dear to you as your own, and the honor of your colleague as the reverence for your teacher, and the reverence for your teacher as the reverence of heaven.

בעצב תלדי בנים תגדלי אותם בצער יותר משאר ב''ח. כי אמנם תאמר מלת לידה על הגידול כאמרו חמשת בני מיכל בת שאול אשר ילד' לעדרי אל בן ברזלי המחולתי:

בעצב תלדי בנים, you will experience anguish while engaged in raising them, by comparison to the other creatures on earth who do not experience such prolonged periods during which they have to look after all the needs of their young.

Rabbi Menachem Mendel of Kotzk

If you truly wish your children to study Torah, study it yourself in their presence. They will follow your example. Otherwise, they will not themselves study Torah, but will simply instruct their children to do so.
Why?
(ד) וַיֹּרֵ֗נִי וַיֹּ֥אמֶר לִ֗י יִֽתְמׇךְ־דְּבָרַ֥י לִבֶּ֑ךָ שְׁמֹ֖ר מִצְוֺתַ֣י וֶחְיֵֽה׃ (ה) קְנֵ֣ה חׇ֭כְמָה קְנֵ֣ה בִינָ֑ה אַל־תִּשְׁכַּ֥ח וְאַל־תֵּ֝֗ט מֵאִמְרֵי־פִֽי׃ (ו) אַל־תַּעַזְבֶ֥הָ וְתִשְׁמְרֶ֑ךָּ אֱהָבֶ֥הָ וְתִצְּרֶֽךָּ׃ (ז) רֵאשִׁ֣ית חׇ֭כְמָה קְנֵ֣ה חׇכְמָ֑ה וּבְכׇל־קִ֝נְיָנְךָ֗ קְנֵ֣ה בִינָֽה׃ (ח) סַלְסְלֶ֥הָ וּֽתְרוֹמְמֶ֑ךָּ תְּ֝כַבֵּ֗דְךָ כִּ֣י תְחַבְּקֶֽנָּה׃ (ט) תִּתֵּ֣ן לְ֭רֹאשְׁךָ לִוְיַת־חֵ֑ן עֲטֶ֖רֶת תִּפְאֶ֣רֶת תְּמַגְּנֶֽךָּ׃ (י) שְׁמַ֣ע בְּ֭נִי וְקַ֣ח אֲמָרָ֑י וְיִרְבּ֥וּ לְ֝ךָ֗ שְׁנ֣וֹת חַיִּֽים׃ (יא) בְּדֶ֣רֶךְ חׇ֭כְמָה הֹרֵיתִ֑יךָ הִ֝דְרַכְתִּ֗יךָ בְּמַעְגְּלֵי־יֹֽשֶׁר׃
(4) He instructed me and said to me,
“Let your mind hold on to my words;
Keep my commandments and you will live.
(5) Acquire wisdom, acquire discernment;
Do not forget and do not swerve from my words.
(6) Do not forsake her and she will guard you;
Love her and she will protect you.
(7) The beginning of wisdom is—acquire wisdom;
With all your acquisitions, acquire discernment.
(8) Hug her to you and she will exalt you;
She will bring you honor if you embrace her.
(9) She will adorn your head with a graceful wreath;
Crown you with a glorious diadem.”
(10) My son, heed and take in my words,
And you will have many years of life.
(11) I instruct you in the way of wisdom;
I guide you in straight courses.
Shir HaShirim Rabbah, Chapter 1, 4:1
When the people of Israel stood at Mt. Sinai ready to receive the Torah, God said to them, "Bring Me good securities to guarantee that you will keep it, and then I will give the Torah to you." They said, "Our ancestors will be our securities." Said God to them, "I have faults to find with your ancestors...But bring Me good securities and I will give to you." They said, "O King of the Universe, our prophets will be our securities." God replied, "I have faults to find with your prophets...Still, bring Me good securities and I will give the Torah to you." They said to God, "Our children will be our securities." And God replied, "Indeed these are good securities. For their sake I will give you the Torah."
יְבָרֶכְךָ֥ יְהוָ֖ה וְיִשְׁמְרֶֽךָ׃ (ס) יָאֵ֨ר יְהוָ֧ה ׀ פָּנָ֛יו אֵלֶ֖יךָ וִֽיחֻנֶּֽךָּ׃ (ס) יִשָּׂ֨א יְהוָ֤ה ׀ פָּנָיו֙ אֵלֶ֔יךָ וְיָשֵׂ֥ם לְךָ֖ שָׁלֽוֹם׃ (ס)

This is the blessing said over children. The Lord bless you and protect you! The Lord deal kindly and graciously with you! The Lord bestow the Lord's favor upon you and grant you peace!

What values should we teach our children, according to Jewish text?
לא לימא איניש לינוקא דיהיבנא לך מידי ולא יהיב ליה משום דאתי לאגמוריה שיקרא שנא' (ירמיהו ט, ד) למדו לשונם דבר שקר

One should not promise to give something to a child and then not give it to them, because that person will thereby teach the child lying, as it is said, “They have taught their tongues to speak lies” (Jeremiah 9:4).

(ט) רַ֡ק הִשָּׁ֣מֶר לְךָ֩ וּשְׁמֹ֨ר נַפְשְׁךָ֜ מְאֹ֗ד פֶּן־תִּשְׁכַּ֨ח אֶת־הַדְּבָרִ֜ים אֲשֶׁר־רָא֣וּ עֵינֶ֗יךָ וּפֶן־יָס֙וּרוּ֙ מִלְּבָ֣בְךָ֔ כֹּ֖ל יְמֵ֣י חַיֶּ֑יךָ וְהוֹדַעְתָּ֥ם לְבָנֶ֖יךָ וְלִבְנֵ֥י בָנֶֽיךָ׃

(9) But take utmost care and watch yourselves scrupulously, so that you do not forget the things that you saw with your own eyes and so that they do not fade from your mind as long as you live. And make them known to your children and to your children’s children.

(י) אַרְבַּע מִדּוֹת בָּאָדָם. הָאוֹמֵר שֶׁלִּי שֶׁלִּי וְשֶׁלְּךָ שֶׁלָּךְ, זוֹ מִדָּה בֵינוֹנִית. וְיֵשׁ אוֹמְרִים, זוֹ מִדַּת סְדוֹם. שֶׁלִּי שֶׁלְּךָ וְשֶׁלְּךָ שֶׁלִּי, עַם הָאָרֶץ. שֶׁלִּי שֶׁלְּךָ וְשֶׁלְּךָ שֶׁלָּךְ, חָסִיד. שֶׁלִּי שֶׁלִּי וְשֶׁלְּךָ שֶׁלִּי, רָשָׁע:

(10) There are four types of character in human beings:One that says: “mine is mine, and yours is yours”: this is a commonplace type; and some say this is a sodom-type of character. [One that says:] “mine is yours and yours is mine”: is an unlearned person (am haaretz); [One that says:] “mine is yours is yours is yours” is a pious person. [One that says:] “mine is mine, and yours is mine” is a wicked person.