Many people are puzzled by the verse: “Train the youth according to his way”, thinking, shouldn’t young, inexperienced children be educated according to the methodical, experienced ways of their parents and educators? But let us imagine two children in the same family, one with a tendency towards stinginess and another with a tendency towards extravagance. The first one takes only for himself, keeps everything he receives, and is unwilling to share with any of his friends or siblings, while his brother gives away everything he owns and never thinks about the future. In such a family, it certainly would not make sense to discuss the importance of sharing with both kids equally, in the same way that it wouldn’t make sense to talk to them about the disadvantages associated with excessive spending. However, both kids do need to hear about the negative sides of both of these qualities, and it is certainly important to emphasize them in conversations with each child while strengthening his weaknesses at the same time.
Moreover, one child may be delicate and sensitive and only require one subtle comment from the parent or teacher expressing disappointment or dissatisfaction, to immediately correct his mistake. While another child may need an explicit and detailed command, as gently hinting to the latter would be ineffective and scolding the former would hurt his fragile character.
And now we can better understand the words of the verse, “Train the youth according to his way”. Meaning, observe and examine the ways of each individual child, both your children at home, and your students in class, and educate them in accordance with their nature and character, this refers to both the topic being taught and the method used to teach it. Only then will you be able to attain the pinnacle of success in education, as in:
“Even when he grows old, he will not swerve from it”; regardless of the situation, its location, or how old he is.
This concludes the simple level of the verse.
The Vilna Gaon zt”l, however, guides us according to the teachings of the Talmud, to delve deeper into the verse so that we may discover a great and important principle in education. In his commentary on the book of Mishlei, he cites the words of the Talmud:
He who is born under planet Mars will be a shedder of blood. R’ Ashi observed: Either a surgeon, a slaughterer, a circumciser, or a murderer.
Are the sages of the Talmud attempting to predict this person’s fortune?
The Vilna Gaon is revealing a great principle and a wonderful guideline in education:
A person with an innate tendency to kill (this can be identified at a young age, as some kids are horrified by the sight of blood while others are curious about it) cannot be changed and transformed into a sensitive person – as the sages state: “He will be a shedder of blood”. But we can definitely channel his personality in a positive direction through kindness, for example, he can take blood tests from patients or become a surgeon, he can fulfill the mitzvah of shchita (Jewish slaughtering) and slaughter animals for people to consume, or perform an even loftier mitzvah and bring his fellow Jews into the covenant of Avraham (as in, circumcision). But if we do not channel his natural inclination in a positive way, he may take the negative route and become a murderer.
In other words, the goal of education is not to change the child’s nature (or our own nature for that matter), even when the personality is seemingly negative. Such an attempt will be unsuccessful and will break the child’s spirit. The role of education is to take any personality type regardless of what it is and channel it in a positive way. This is the reason the sages have always made sure to use the term good/bad midot (translated as character traits but literally means ‘measures’) as opposed to a good or bad personality etc. as each feature and personality type can be directed in a beneficial way where it can be advantageous and desirable, as long as it is used in the proper measure. And if it is applied according to the values of G-d’s Torah, it is referred to as a good mida and the outcome will be favorable, if not, it is considered a bad mida. This is what “Train the youth according to his way” actually means – according to his unique personality. By doing so, you can teach the child how to successfully and independently overcome the challenges of his life.
Therefore, one of the basic rules in education is: to provide support while leaving some room for trial and error. Giving too much freedom to the child creates a gap between the parents’ instruction and the child’s obligation to implement it. On the other hand, complete dependence on the parents trains the child to respond in a robotic way according to the will of the parents without him internalizing these matters and performing them consciously and independently. Therefore, it is important to always leave the child some room to deal with life’s challenges on his own so he can apply what his parents and teachers have taught him.
For example, when a child asks for help with his homework and has a difficult time preparing it, his parents must take the initiative and intervene. The parent should not dictate the answers to the child, but rather help him find them quickly by giving him a hint towards the correct answer, or show him where to find it. If a child’s room is messy and is beyond his ability to clean it up, the mother should not do the job for him, she should rather help him clean it up as part of a joint effort. A father should not drive his child wherever he wants to go, rather he should help him figure out how to reach his desired destination on his own. This should all be done of course in accordance with the child's age and his level of competence. Even when developing the child’s thinking skills, it is important to make sure he can think for himself. Here’s an excerpt from the wonderful book entitled, “The Tent of Yaakov and Leah”:
A parent must answer the child’s questions, and not reply by saying, “you’ll understand when you grow up”. A child’s curiosity is a spark of an adult’s quest for knowledge. When a child grows up in a strange and unclear environment, the light of his mind begins to dim and knowledge becomes unnecessary in his world. If he later becomes disinterested in his studies, we should not be surprised. The development of his mind begins at childhood. He must be given simple explanations regarding things that concern him. He should be informed of the events that take place around him and not be led through a world that is clouded and obscure. A child feels deeply connected to the happiness or G-d forbid, sadness experienced by his family, and wishes to understand its meaning. If the child is not given a sense of partnership through explanation and discussion, his feelings are badly hurt, and a dangerous distance is created between himself and his educators.
It should be noted that although a child must be kept away from bad influences where unclean speech or immodest dress is prevalent etc., if a child happens to be exposed to such indecency by accident, it must be taken advantage of and used to strengthen him. This may be achieved by means of short but sharp words expressing disapproval and total rejection of this vulgarity, reminding the child that we don’t speak this way and that we choose to maintain the cleanliness and sanctity of our speech. And with regard to dress, we should mention the virtue of man in contrast to animals. The more a person connects to his “humanness” the more modestly he feels he needs to dress. At the appropriate age it would be relevant to teach the child that the word l’vush (dress) can be read as lo bosh (without embarrassment), as a person who maintains his ‘human’ level and does not descend to the animal level, is embarrassed by walking around with his body parts exposed. His l’vush (dress) spares him from embarrassment – lo bosh.
Because of the esteemed positions they hold in the world, women should be extra careful with this quality, as even some non-Jewish women avoid dressing immodestly and feel that this form of dress is disgraceful to human dignity.
If this is the case for some non-Jewish women, then all the more so for a Jewish woman, as it was said: “Every honorable princess dwells within”. And one need not worry about making fun of immodest dress, as it falls under the category of “All joking around is forbidden, besides for when it concerns idol worship – then it is permissible”.
On the other hand, when a child encounters a Jew who desecrates Shabbat, he must be taught to view this Jew as ignorant, and not be given permission to mock him. It must be explained to him that unfortunately, some Jews were never educated and are therefore unaware of how important Shabbat is in the eyes of G-d. They are also unaware of how delightful it is and eternally rewarding it is to those who observe it according to Jewish law or conversely, how much they can lose out by desecrating it both in this world and in the world-to-come.
Notes and Sources
 Mishlei 22:6
 Mishlei 22:10
 Shabbat 156a
 Ohel Yaakov V’Leah p.35
 Tehillim 45:14
 Megilla 25b
Adapted from “The Keys to Life” by Rabbi Zamir Cohen