The rule of “educate your child according to his way” does not at all imply permissiveness. On the contrary, it is a very strict approach.
“According to his way” means in accordance with the child’s inclination. If a child has a talent for math, put him into a math school and force him to study using all means possible. And if someone has a talent for dancing, let him take ballet classes and do it seriously. “According to his way” does not mean “whatever the child pleases.” If not, where is “educate your child?”
Children should be given only positive examples. After all, we are born with the egoistic nature, as it is said by the Creator: “I created the evil inclination.” No good inclination was created against it, but rather, only the reforming Light which can be attracted by Kabbalah studies.
Hence, when we show a person something bad and say that it is not good to behave this way, he does not agree: “It’s bad, but I want it!” He does not connect the words with actions: He says that it is bad, but does it.
For this reason, it is not advisable to give children negative examples along with positive ones so that they could choose. They will never choose good. They will follow their nature and always be attracted to bad examples and actions in spite of numerous sermons. On the contrary, by seeing only positive examples and discussing them in various formats, we gradually transition to good. Habit becomes a second nature.
What can be considered a positive example? A person sets an example by being strongly connected to the group, inspiring his friends, and acting together with them.
Children should know how to evaluate themselves with respect to the group and their own actions. For this, they need to be given a scale of achievements since otherwise a child does not know how to assess his acts. Bestowing to the group has to have an external form which could be used as a measuring instrument.
From Daily Kabbalah Lesson 12/3/10, Talk on Education