Helping Our Kids to Embrace Disappointment

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A woman disappointed holding her knees.There’s a lot of talk out there about setting kids up for success. There are numerous medals and accolades awarded for simply showing up. And showing up is half the battle. But a great deal of the battle also involves dealing with disappointment. That is not only a universal truth, but it is also a part of life. It should be as much a part of our dialogue with our children as the “pump up.”

Disappointment, rejection, not being chosen, not winning, not making the cut, not getting it —however we wish to characterize it —is simply a significant component in the alchemy of our existence.

I don’t care who you are, where you’re from, how attractive or popular you think you are, or how much money you have. We grownups know the feeling of not being enough. And our natural instincts are to want to protect our kids from experiencing that pain. We cannot.

It doesn’t matter how much we praise them or how much we give them. Disappointment is simply a fact—a necessary fact—of life. I feel like there is a generation of parents (myself included) who think it is their responsibility to shield their children from disappointment.

Aside from the fact that we can’t do that, I believe it actually backfires and only leads to a much deeper sense of failure in our children.

Our kids are amazing in every way, but they will not always be recognized for their special amazingness. They just won’t. And that’s not necessarily a bad thing. In fact, some of my own greatest triumphs were born from failure.

There are not only lessons in disappointment, but also huge opportunities.

We learn how tough we are. Or we learn that one path wasn’t meant to be and move on to other, much more fulfilling and authentic ones. Some folks take longer than others to work through disappointments and letdowns, and that’s ok. But the sooner we accept these dips in the road as totally normal and necessary, the less the sting and the sooner the rebound will occur.

Whenever one or both of my kids encounter something disappointing or painful, I try not to react from the space of profound protectiveness or fear in my heart. There’s a much bigger picture than whatever the instant of sadness presents. It’s not to deny the disappointment because that is so very real at that moment. But there’s so much more than the immediate situation and knee-jerk reaction.

There’s a whole life of letdowns that shape us and will shape them in a way that triumphs never can.

I tell my kids that I have absolute faith that they will find their way, that their struggles will eventually become their greatest teachers. And I mean it, even though I wish from the bottom of my heart that it didn’t have to work that way.

Struggle is the essence of humanity. If we accept this as adults, why not encourage our children to do the same? The best message to send them is that they’ve got this, whatever the “this” is. Even the parts that seem not to be working out. 

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Jordana
Jordana lives in Bedford Hills, NY, with her two favorite humans also known as her children, Kaylie (13) and Chase (12). She grew up all over the world, landed in the Washington D.C. area for a long stretch and 15 years ago wound up in Westchester, which she now proudly considers home. She's a recovering attorney, now assistant to a private wealth advisor. She spends what little free alone time she has on her Peloton, watching reality and crime TV and listening to a wide variety of music on her deck with a cocktail. She enjoys taking her kids for day trips into New York City, local restaurants in the Hudson Valley, beach vacations in Rhode Island and the occasional amusement park But she also loves just hanging out and relaxing with them at home. She loathes laundry, grocery shopping and vacuuming. Jordana's favorite mottos to live by are don't compare yourself to anyone else (especially when it comes to parenting), don't be afraid to take chances or start over, always strive to be kind, and never take yourself too seriously. And if all else fails, have a good scream into your pillow, and go do something really nice for yourself, or better yet, somebody else.