It is common custom within the Torah community to begin training a child in his observance from the earliest ages. Nevertheless, at a very young age, a child lacks the maturity that would enable the educational process to be carried out in a steady, consistent, and firm manner. To put it in practical terms: a child may be given a yarmulka to wear at a young age, but there are times that he will refuse to wear it. Before his upsherinish, a parent may chose to bypass the issue at times. After the upsherinish, that choice should not be made. Instead, the yarmulka should be considered an integral part of his being. Similarly, in all matters of education, the upsherinish should be the age where a systematic and determined program of education begins.

The letter from the Previous Rebbe to which the Rebbe would always refer with regard to an upsherinish1 alludes to such an approach, stating: “From the day of the haircut [when] peyos are left, it is customary to carefully train the child to wear a tallis kattan and to recite the morning blessings, the Grace after Meals, and the Shema before retiring.” Implied is that some training may have gone on previously, but “careful” training begins from the upsherinish.

To refer to some of the specific points mentioned in that letter: From page 2 of Siddur Tehillat HaShem, it appears that the intent is not to recite the entire morning blessings, but rather Modeh Ani, the blessing over washing the hands, the verse Torah Tzivah, and the first paragraph of the Shema. For Grace, the intent is not the recitation of the entire Grace, but the statement Brich Rachmana. And for the Shema upon retiring, the first paragraph of the Shema and the verse: Biyadcha afkid ruchi should be recited.

With regard to tzitzis, a child may be trained to wear tziztzis before his upsherinish. (The Previous Rebbe was trained from the time he began to walk.)2 From the upsherinish onward, he should be comfortable with wearing the tzitzis and committed to doing so at all times.

Similarly, with regard to other matters, the upsherinish marks a turning point. For example, with regard to wearing a yarmulka, children should be trained to begin doing so much earlier.3 (The Rebbe Rashab wrote that the Previous Rebbe wore a yarmulka from the day of his bris.) From the upsherinish onward, however, extra emphasis should be placed on the matter. Also with regard to Negel Vasser, the morning washing, in his Shulchan Aruch HaRav,4 the Alter Rebbe writes that a child’s hands should be washed from his bris onward. Nevertheless, from the age of three onward, one should be meticulous about the matter.5