Aish.com has a wonderful discussion about the depth and breadth of this commandment...
Ki Tetzei (Deuteronomy 21:10-25:19)
Fundamentals of Education
by Rabbi Zev Leff
"When a man has a wayward, rebellious son, who does not obey his father and mother, they shall have him flogged. If he still does not listen to them... [the parents] must declare to the elders of his city, 'Our son is wayward and rebellious. He does not listen to us, and is an (exceptional) glutton and drunkard.' "(Deut. 21:18)
The Talmud (Sanhedrin 71a) says that there never was a rebellious son executed by the court. The topic was recorded in the Torah in order to learn and receive reward. But even if there never was a rebellious son, we can learn a great deal about raising children from a careful study of the Torah's description of the rebellious son. By studying the factors that help create a son so tainted that it is a kindness to kill him while he is still young and has not yet committed all the heinous crimes he otherwise would, we can learn to do the opposite with our own children.
It must be clear at the outset that there are no sure-fire rules of education that apply to all children at all times. Reishis Chachmah quotes a Midrash that it is easier to raise a legion of olive trees in the Galilee, where the soil and climate are not conducive to growing olive trees, than to raise one child in the Land of Israel, even though Israel is conducive to proper education, since the atmosphere itself helps to imbue one with wisdom and holiness.
Children are not objects to be fashioned at will, but rather human beings who have their own free will and can reject, if they so choose, even the best education. The most a parent can hope to achieve, as Chiddushei HaRim points out regarding all learning, is to put the words of Torah on the heart of the child so that when the heart opens up, the Torah found on it will sink into the receptive heart.
STRONG ROOTS
The law of the rebellious son is applicable only when the child is age 13 and for the next three months, i.e., at the very inception of his manhood. This points to the importance of a proper foundation in the education of children - that early education forms the basis of the child's experience and hence is the root and foundation of his life.
Avos deRav Nosson expounds on the Mishnah (Avot 4:25), "One who studies Torah as a child, to what can he be likened? To ink, written on fresh paper." Just as ink is readily absorbed into new paper, so the Torah learned when young permeates the very fiber of the child's being.
Alshich explains the injunction (Proverbs 22:6), "Educate the youth according to his path," as a warning to put him on the proper path before he develops the wrong path on his own. The proper beginning is crucial, for it forms the root, and any blemish in the root will manifest itself a thousand-fold in the resultant growth. A strong root, however, insures a healthy plant.
FOLLOWING INSTRUCTIONS
The Torah describes the rebellious son as not heeding the voice (kol) of his father and mother. Maharal points out that a kol denotes a voice or noise, something not necessarily intelligible. The rebellious son listens to his parents when their words make sense to him, but when their directives are not understood by him, he ignores them.
A child must be taught to rely on his parents' instructions and trust in their desire and ability to guide him on the proper path, even though he may not understand or grasp the wisdom of their directions. Though a parent should try to explain to the child the reasons for his directions and instructions, the child must be taught that in the end whether he understands or not, he must accept his parents' authority.
The Talmud learns from the phrase, "he does not listen to our voices," that to be deemed a rebellious son, both parents must have similar voices. Both parents' guidance must reflect the same values, and they must be consistent in their instruction. If the parents do not speak with one voice, their child cannot be deemed rebellious, because the blame for his rebellious behavior is not his alone.
Further, the parents must point at their son and say, "this son of ours." If the parents are blind and thus incapable of pointing him out, the son cannot be deemed a rebellious son. The requirement that the parents be able to see hints to the necessity of parents viewing each child as an individual, with unique gifts and needs, who must be educated according to his individual personality. If parents are blind to the child's individuality and educate him according to a predetermined formula, the child can also not be fully blamed.
SPIRITUAL STATUS
To be classified as a rebellious son, he must steal money from his parents to eat and drink like a glutton. This conduct shows, says Ibn Ezra, a distorted outlook. The glutton makes the pleasures of this world his only goal rather than seeing this world as the place to prepare for eternal spiritual life. The meat and wine he consumed could have been fully kosher. It is not enough to teach a child that he may eat only kosher food. He must also understand why, so that he does not become a Jew in form but not in substance.
The Talmud explains that the rebellious son is killed now, because if allowed to continue on the same path he will eventually become a robber and murderer. He is killed for his own benefit so that he doesn't lose his portion in the World to Come.
From this we learn the most important lesson of child-rearing. A parent must focus on the soul of his child and his eternal status, even more intensely that his physical well-being. What parent would think of exposing his child to even a slight chance of catching a serious communicable disease? How much more so should a parent protect his child from an environment that might exert negative spiritual influences. If we fret over our child's ability to earn a living, how much more so should we be concerned that he or she grow to be a successful Jew.
We should remember in Elul that there is no greater merit for the Day of Judgment than having raised a child properly. The Zohar teaches that when an individual appears before the Heavenly Court, after 120 years, God inquires if he educated his children properly. If the answer is affirmative, God refuses to accept any more testimony against him, for the merit of guiding his children properly overshadows everything else.
May we learn the deep lessons contained in the Torah's discussion of the rebellious son, so that we merit to raise children fully occupied in Torah and mitzvot.
