Kenny is a silly, skinny, blue-eyed, nine-year-old boy, who barely tips the scales at 48 pounds. “I can practically spit through him,” my dad says on a regular basis.

Although Kenny showed promise on the rec league baseball field last spring, his performance didn’t cause anyone to spill their beer. When his BFF, Jim, a baseball prodigy – built more like a tree trunk than a twig – announced he was planning to try out for an elite travel team, Kenny jumped on the bandwagon. The tryouts were open, and Kenny wanted to sign up.

“Ugh,” I thought.

“He’ll get killed!” a neighbor exclaimed when he heard the news.

The line between setting a child up for success and protecting him from disappointment is hazy. Parents never want to see their child hurt or disappointed. After all, it might lead to him quitting or giving up. Yet the alternative – attempting to shield him from life’s inevitable sprinkling of disappointments – is not only impossible, but it also backfires.