In the most recent edition of Jewish Action, there was an article called "Taking the Plunge" by Ann Koffsky, discussing the concept of a father being obligated to teach their child to swim.
As a lifeguard, she is the one who helps parents fulfill that requirement. To a child, she says, whatever she is telling them is madness. They know the laws of nature by now. They understand gravity and the choking sensation water can provide. Now there is this crazy woman telling them to ignore all that hard-earned knowledge.
But when they finally decide to give in out of good manners, they feel accomplished. They tried something, and they conquered it.
Perhaps that is what the Gemara is trying to teach us as parents. If it was to just keep our kids safe, the best advice would be “Make sure your kids stay away from water.” But that is not the Gemara’s approach. Perhaps the major lesson the Gemara wants us to teach our kids is to overcome fear and just get in the pool. To live life, not avoid it. Because once you get past all that fear—swimming is really fun! It’s there for us to enjoy.
Today's parents sometimes go the extra mile to shield their children from "questionable" influences, even well after marriage and having their own kids.
Ma phrased it like so: "They think their child will go out there and slip on the first banana peel?"
May we all learn from these kids and overcome that which is holding us back in our own lives, whether it’s trying to learn something new even though we fear looking ignorant, or doing chessed even if we fear failure, or reaching out to an estranged family member despite our fear of rejection. We must learn to overcome and take the plunge.
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