“What should we do when our child doesn’t want to learn? The Gemara answers: “In Usha they established that a man should ‘roll’ with his child until twelve years of age, and then get tough with him.’ What does it mean to ‘roll’ with one’s child? Rashi explains: ‘If he doesn’t want to learn, ‘roll’ pleasantly with him, with soft words.’ Persuade him. Entice him… Of course, today the age has changed, and what was once only appropriate until age twelve is now appropriate until age twenty. Until age twenty we must ‘roll’ with our child.”
-Rabbi Shlomo Wolbe, PLANTING AND BUILDING, p. 65
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