12/18/2013 06:42 pm ET Updated Feb 17, 2014

Why It's Good for Kids to Be Disappointed (Sometimes)

Rachel Levy Lesser

My childhood bedroom had no trophies in it. It wasn't for lack of trying. I played sports and entered the swim races at our pool every summer. I was an average athlete. Not the worst, but certainly not the best. And so I never got any trophies. That's how it went.

My children's rooms are overflowing with trophies. We had to clear out some of my son's from a few years ago to make room for the new ones that he gets every season for whatever sport he plays. And my daughter's bedroom door makes that clunking noise every time you open and close it due to the countless medals hanging from the door knob. They are good athletes. Not the worst, but like me, also not the best.

It's just that accolades seem to come easier these days. Every kid has some kind of participant medal or at least a certificate somewhere. I am all for boosting children's self-esteem -- especially when it comes to my own kids, but I also think they should know what disappointment feels like and learn how to deal with it.

My late mother felt the same way. When my brother and I were growing up, she let us experience those challenging situations and "stick it out" or "buck up," as she used to say.

"It will make for good dinner party conversation one day," she told my brother when he called home collect in misery from a British boarding school where he was spending a year as an 18-year-old kid. He wanted that year away and although it turned out to be not at all what he had pictured, he was told to "stick it out" and he did.

And do you know what? It has become great dinner party conversation. So, too, has the story about how I chose to take the SATs a second time because I was disappointed in my first scores. Well guess what? Despite all of my studying and good intentions, my scores actually went down the second time and they counted! And I had to live with them. I called my parents in tears, and I was told to "buck up." I didn't really have a choice. My family really likes to tell that story. It's a good one at any dinner party.

My mom was very loving and caring and so is my dad. We were and are very close. They were about as far from mean as you could get, but they knew that it was important for kids to understand that things won't always go their way and to adjust to these types of circumstances. I try to pass on these important lessons to my own children, but it's tough today.

They always make the teams because everyone makes the teams! I didn't. I had to spend a summer making a candle (dip the wick in the wax and go to the end of the line) while my brother and cousins played on the softball team at the community center. My own cousins didn't pick me for their team and guess what? That's a great dinner party conversation. Just ask my husband. He loves that one.

I guess I am struggling to find that fine line between making sure that my kids feel good about themselves but also know how to deal with some of the not so pleasant stuff that life will surely throw at them. I think it's in these experiences of dealing with the disappointment that will make them stronger and ultimately happier, more well adjusted kids and adults.

And these experiences will certainly give them years of good dinner party conversation. After all who wants to go to a dinner party where all everyone talks about is how they made every team and got every award? I certainly don't.