Holidays are a most opportune time to instill in our children the values and character traits that personify a Jewish lifestyle. At first glance Pesach, more than any other holiday, seems to embody the critical importance of teaching our children. The entire seder is focused on children of all types and stripes; the intense preparation for the holiday and the excitement of the seder make it a most memorable one for children. The Torah's description of Pesach centres on such imperatives as, "and when your children ask", "and you shall teach your children", and "when your children say".
Nonetheless, upon closer analysis, it appears that Sukkot plays an even more crucial role in teaching our children and ensuring their understanding of the mitzvot. "You shall dwell in the sukkah for seven days. All citizens of Israel should sit in a sukkah, so that future generations will know that I had the Israelites live in sukkot when I brought them out of Egypt" (Vayikra 23:42). It is Sukkot, not Pesach, that the Torah links to the teaching of future generations. This knowledge of why we sit in the sukkah is so crucial that according to many authorities (see Bach, Orach Chaim 625), one does not completely fulfill one's obligation if one does not understand why we perform this mitzvah, a feature we find in few other mitzvot. What is so special about Sukkot?
Pesach is the holiday that celebrates the remembrance of our past. It is the time to relive the Exodus, and to celebrate our great historical longevity and survival. While many arise to destroy us, we, the Jewish people, continue to thrive and survive.
A shared memory is crucial in developing a nation. Nonetheless, memory in and of itself cannot sustain a tradition or a people. Many Jews today have fond memories of an observant past yet have no desire to take upon themselves the yoke of commandments. It is difficult to transmit the essence of memory to the next generation. What we may recall with fondness, contemporary Jews often see as relics of a distant, irrelevant past. To inspire our children, we first must give them knowledge. Holocaust memorials may keep the memory of our past alive, yet it is Jewish education that will ensure our future. The biblical holiday season begins with Pesach and concludes with Sukkot. We move from the past to the future, a future in which the sukkah of peace will be spread upon us.
Interestingly, many of the laws of chinuch, educating our children, are to be found in the Talmudic tractate Sukkah. This is no coincidence; the Talmud was edited with meticulous care, and its wide range of topics discussed, both legal and extra-legal, were organized with great precision into its 63 tractates. Thus, the stories relating to the destruction of the Beit Hamikdash are to be found in masechet Gittin which focus on the laws of divorce, as our exile represents a form of divorce from the Almighty. Conversely, the special status of the land of Israel is discussed in masechet Ketubot, which discuss the laws of marriage, with the return of the people of Israel to the land of Israel symbolic of the marriage of G-d and the Jewish people.
In addressing the proper age to begin training children in the observance of particular mitzvot, the Talmud (Sukkah 42a) teaches that one should teach children about mitzvot only when the child can properly perform the mitzvah in its complete form. For example, only when a child knows how and when to shake the lulav is he required to shake it, despite the fact that such shaking is not integral to the mitzvah. There is little point in training a child to do a mitzvah incompletely; better to wait a while and get it right.
This message is a crucial one in educating our children. All too often, parents make decisions that are in their own best interests, but not necessarily that of their children. We like to boast of our children's knowledge and exposure to subject material that they are not fully capable of understanding. This can have serious long-term negative ramifications. It would be much wiser to wait a few years until the analytical ability of the child is ready to grasp such material.
Masechet Sukkah begins by recounting the visit of the Sages to the Sukkah of Shlomtzion HaMalka. She was insistent that her children not be allowed to sit in an invalid sukkah; better to eat in the house, she felt, than in an improperly built sukkah. The tractate ends with the tragic story of the Bilga family. This family of kohanim was punished for the misdeeds of one of their children. The Sages of the Talmud tried to understand the justification for the punishment of parents for the indiscretions of their children; after all, the Torah instructs us that “parents shall not be put to death for the sins of their children” (Devarim 24:16). The Talmud explains, “The speech of a child in the marketplace is derived either from that of his father or from that of his mother” (Sukkah 56b). Children, especially young children, innocently repeat what they hear at home.
The sukkah, like life itself, can be very flimsy and insecure. It is, by definition, temporary. Our only guarantee for Jewish permanence is by properly educating the next generation of Jewish children. This is a job that allows for no short cuts. But it is a job that, done properly, brings great joy. May we merit to properly fulfill this most sacred of tasks.
 One need not have biological children to fulfill this mitzva. "'And you shall teach your children'—these are your students" (see Rashi, Devarim 6:7). Some of the greatest teachers of recent times - The Lubavitcher Rebbe, The Chazon Ish, Nechama Leibowitz, Rabbi Saul Lieberman, The Sreidei Aish, did not have biological children. Whatever our walk of life, we have many opportunities to teach.