Photo Credit: Rifka Schonfeld

Gershon got up from the chessboard and walked away slowly, pouting as he headed to the bathroom. His father watched him go and once again wondered if he had made a mistake in playing competitively against his son. Gershon hated to lose, but how could he improve if his father always let him win?

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The question of whether we should be shielding our children or exposing them to the realities of the world is a hot topic in parenting today. There are some parents who believe in pushing their children to the limit of their abilities. If their child receives a 99, they ask where the other point went. If their child hits a homerun three times in a game but strikes out during his first time at bat, they want to know what went wrong and insist he practice his swing when they get home. These parents believe that their children are strong enough to withstand significant criticism.

Then there are those parents who, ever fearful of destroying their children’s self-esteem, are careful with each word they utter. These parents applaud even a child’s mistakes, never letting him or her feel the least bit of disappointment. They tell their children that Ds in school are okay as long as they tried their best and that A’s for effort are the most important element on the report card. Their children can do no wrong.

Obviously, there is a middle ground. But, in reality children do need to occasionally experience disappointment and failure in order to understand how to overcome it. Dr. Wendy Mogel, in her book, The Blessing of a Skinned Knee: Using Jewish Teaching to Raise Self-Reliant Children writes about the importance of balance in Jewish parenting:

Parents’ urge to overprotect their children is based on fear – fear of strangers, the street. Fear of the child’s not being invited to the right parties or accepted by the right schools… Real protection means teaching children to manage risks on their own, not shielding them from every hazard… Children need an opportunity to learn about the “wave-pattern” of emotions. If parents rush in to rescue them from distress, children don’t get an opportunity to learn that they can suffer and recover on their own.

Here, Mogel asserts that children need to fail in order to understand that they can survive failure and recover.

But, what does this have to do with playing games with your son? Letting your son win is protecting him from failure (and, I’d assume also takes much of the fun out of the game – for him as well as you!) On the other hand, allowing him to feel triumphant every now and then can help boost his self-worth.

So, the answer to your question is: win a little and lose a little. Try to play games that even the playing field – ones that you are not particularly skilled at. Your child can’t always win – but you don’t need to keep knocking him down either. He will gain self-esteem from his successes and he will learn to handle failure from his losses. The Rambam speaks about the shvil hazahav, the golden mean, and that’s exactly what you should aim for!

Transforming the Negative into Positive

Another element of Mogel’s book worth noting is her focus on turning the negative into a positive. So, what happens if your son hates losing? This irritating quality might actually be something good for him in the future. In her book, Mogel devotes a chapter to “Channeling Your Child’s Yetzer Hara.” In a nutshell, she asks parents to identify their child’s worst or most irritating trait and then encourages them to “reframe” it as a positive attribute.

For instance, Mogel presents a mother who describes her daughter Lucy as: “unbelievably bossy…Her preschool teachers says that Lucy doesn’t paint but prefers to walk around the room reminding the other children to put on their smocks, not to mix colors, and to shake off their brushes so the paint won’t get too watery. She is constantly organizing and fixing…”

Her mother is frustrated by her forcefulness and her lack of good manners. However, what she fails to see is that there are positive ways for Lucy to use this “negative” attribute. Instead of viewing Lucy’s behavior as bossy, she can view it as demonstrating leadership skills. In addition, her organizational skills can come in very handy when keeping her room clean or doing chores around the house.


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An acclaimed educator and social skills ​specialist​, Mrs. Rifka Schonfeld has served the Jewish community for close to thirty years. She founded and directs the widely acclaimed educational program, SOS, servicing all grade levels in secular as well as Hebrew studies. A kriah and reading specialist, she has given dynamic workshops and has set up reading labs in many schools. In addition, she offers evaluations G.E.D. preparation, social skills training and shidduch coaching, focusing on building self-esteem and self-awareness. She can be reached at 718-382-5437 or at [email protected].