More importantly, though, instilling self-esteem should not be the goal of parenting. Indeed, according to Judaism, self-esteem is a rather bad trait to possess. One is not supposed to esteem oneself. “Be of exceedingly lowly spirit,” Pirkei Avos states. According to the Rambam, humility is one of only two traits for which one should abandon the golden mean. “If a man is only humble,” he writes, “he is not following a good path. Rather, he must hold himself lowly and very unassuming.”
The Ramban, in his famous letter to his son – published by ArtScroll as A Letter for the Ages – spends fully half of it urging his son to be humble, which he calls “the finest of all admirable traits.” He says man is “as frail as the maggot or the worm” and instructs his son to let “all men seem greater than you in your eyes.” He should “learn to stand meekly before man, and fearfully before God” since, as Mishlei teaches, “On the heels of humility comes fear of Hashem.”
In more recent times, Abraham Joshua Heschel writes, “A religious man could never say: ‘I am a good person.’ Far from being satisfied with his conduct, he prays three times daily: ‘Forgive us, our Father, for we have sinned.’”
Indeed, all this is obvious. Judaism never encourages feeling good about oneself. In no mussar work or classical Jewish work of any kind is self-esteem emphasized. Nowhere in davening do we say, “I’m good enough,” as one popular Jewish organization urges its members to shout. Not only is self-esteem not accorded the prominence given to it today, it’s barely even mentioned in classical Jewish literature – if at all.
Judaism is all about our duties to God and others. It is not about the self, and esteeming oneself is the opposite of what a Jew (or any human being) should feel. That’s why Judaism requires us to start the day with “Modeh ani – Grateful am I” rather than “Ani modeh – I am grateful.” The first word we utter in the morning should not be “I,” explains the Alter of Slabodka. Our modern-day “obsession with me” is nothing less than “the avodah zarah of our time,” Rabbi Jonathan Sacks said in a recent lecture.
So let us not be confused by the self-esteem craze or parenting theories concocted by theoreticians in the 1960s. These theoreticians have sent us down “a road never traveled, leading nowhere,” as gadfly psychologist John Rosemond puts it. Let us return to the chinuch practiced by the older generation – the one that produced respectful children rather than obnoxious ones, the one that emphasized obedience and derech eretz rather than self-esteem, the one that cared about how kids acted rather than how they felt, and the one that produced a generation of fine menschen rather than the increasing number of unpolished adults walking the streets today.