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While watching a children's baseball game in Toronto, I overheard a conversation that sounded as if it emanated from the Billy Crystal comedy Parental Guidance. The film casts a humorous light on over-protective parenting practices. Not unlike the film, each child in this game received a turn at the plate every inning, regardless of the number of outs, provoking the game's observer to shake his head in disbelief.

I get his point. Life is a competitive sport and it serves everyone well to learn how to lose or fail with grace. Failure is good, or so goes the common belief, since it leads to personal and professional development. But I worry that we've gone too far in applauding failure.

Rarely a day goes by where I don't come across a headline or online posting that celebrates failure in some way. While I agree that it can serve a higher purpose, I am skeptical that failure is always a good and necessary part of our development. Sometimes, failures just hurt and we need to mourn them before moving on.

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My ambivalence about failure may be a Canadian trait, according to Roger Pierce, a serial entrepreneur who now runs the Toronto-based firm Pierce Content Marketing.

"In Canada, it seems we are ashamed of failure and feel it forever labels us in a negative light," he said. In the United States, failure – especially among successful entrepreneurs – it is more like "a badge of honour."

"In most rags-to-riches entrepreneur success stories, you'll inevitably find a section about past failures and overcoming seemingly insurmountable obstacles. [Americans] love that story arc," Mr. Pierce said.

This idea recently appeared in Lewis Schiff's Business Brilliant: Surprising Lessons from the Greatest Self-Made Business Icons. Mr. Schiff, executive director of Inc. Business Owners Council, a U.S. membership organization for entrepreneurs, highlights seven principles that separate the super rich and successful from the average lot, including "nothing succeeds like failure."

"Self-made millionaires are more apt to experience failure the way we might experience going to the dentist. It's uncomfortable but inevitable. And it's essential if you want to reach your goals," Mr. Schiff said in an interview with LinkedIn.

But what if all failures can't be turned into valuable life lessons? Barry Moltz, a Chicago-based author, speaker and small business consultant argues that, "Failure stinks when we are going through it and sometimes there is nothing to learn." The business world loves to talk about great comebacks, he noted, cautioning that celebrating failure is a placebo to make us feel better.

"My advice when you fail: Learn what you can, grieve the loss but then let go and take an action that gives you another chance at success," Mr. Moltz said.

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Not only are some failures meaningless, they do us a disservice when we hoist them on a pedestal, according to Lori Buresh, a small business owner and consultant in Missouri. She believes we hurt our chances at future success when we extol failure.

"The thrill of victory is a powerful motivator to continue to win, but losing or failing can be an even bigger motivator to do better. When we remove the opportunity to feel the sting of defeat, we stop striving to get away from it. In a way it is like giving in to fear," she said.

Ms. Buresh isn't the only one expressing caution about the admiration for failure. Daniel Isenberg, a professor of management practice at Babson Global College in Massachusetts, warns against a "cult of failure," in a Harvard Business Review posting, where he worries that this habit is a ploy used by entrepreneurs to mitigate their anxiety.

Art Papas, chief executive officer of Bullhorn, a Boston-based global leader in recruiting software, recently wrote in the Harvard Business Review that "failure is a great teacher, but its lessons are too harsh." Failure, he explained, has the potential to chip away at your self-confidence and if it leads you to become fearful of innovating, "you haven't just failed, you've become a failure."

So how do you navigate that fine line between failing and being a failure? For some, it's simply the ability to roll with those punches and bounce back quickly.

Debbie Dickerson, a business development coach in Houston, said she can count many failures, but one that stands out involves a recent fumbled sales call. Her "victory" came later when she asked a potential client for one more shot, went back in and won the sale.

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"As far as failures go, I try to learn at least one positive from it," Ms. Dickerson said. "I truly do not celebrate failure. [But] if I didn't turn it into a positive I would be a miserable, bitter person."

Leah Eichler is founder of r/ally, a mobile collaboration platform for enterprises. E-mail: leah.eichler@femme-o-nomics.com

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