Should you teach your kids to fail?

Last week, I was at a friend's house chatting about our kids' upcoming extracurricular activities—her kids play hockey, mine take swimming lessons. Our sons were sitting on the couch playing with Lego and, as little kids are wont to do, they eavesdropped on our conversation.

"I'm not sure I want to put Isaac in swimming right now," I confessed. "I don't know if he's strong enough to pass."

"I'll just fail again," Isaac moped from the couch.

"What does fail mean?" my friend's son asked, blank-faced and dead serious.

At this, my friend and I burst out laughing. That particular "F" word isn't a part of their family's vocabulary. Her boys are uber-determined, talented and resilient and haven't yet experienced the discomfort of failure.

Read more: Why I'm happy my kids failed swimming lessons>

As a free-range parent, I pride myself on letting my kids take risks and fall down, so the fact that I've considered pulling my son from swimming lessons on the off-chance he might fail is a change to how I parent. But the negative self-talk that started after Isaac failed his last round of swimming lessons was unexpected and made me feel very sad for him—especially since I consider him to be quite resilient.

Could learning to fail help my son? That's the thinking behind a new trend in conferences, books and courses that teach adults how to navigate the feelings that come with failing. Elizabeth Renzetti highlighted such initiatives last week in the Globe and Mail. Stanford University has launched a resilience project, Toronto hosted Fail Forward in July and the conference FailCon is a worldwide phenomenon, teaching attendees to embrace and learn from failure. Will these types of initiatives find their way into our children's classroom soon? And if so, would successful completion be recognized with an A or an F?

Read more: Kids and failure: When size holds them back>

I'm of the mind that learning from mistakes is like any other developmental milestone. I can't tell you how many times my son fell off his bike before he mastered the skill, or all the words he stumbled over before developing a love of reading. My husband and I keep the language around learning new skills positive—and we tell him we're proud of him, no matter what. The last thing I want my kids to feel is anxiety, which I'm sure is what feeds Isaac's negative thinking. That said, I 100-percent agree with the swimming instructor who flunked him, and appreciate that there are no trophies just for showing up at the pool—a welcome departure from the disturbing trend of youngsters who assume that winning is part of every game.

As for those swimming lessons, Isaac is signed up again. Because to me, the most important life lessons learned from failure are patience, positivism and persistence. And those character traits can't be taught in a classroom.

Follow along as Jennifer Pinarski shares her experiences about giving up her big city job and lifestyle to live in rural Ontario with her husband, while staying home to raise their two young children. Read more Run-at-home mom posts or follow her @JenPinarski.