09/11/2013 07:50 EDT | Updated 11/11/2013 05:12 EST

Oh, You Failed? Maybe You Just Weren't Good Enough

Over the summer, while watching a children's baseball game in Toronto, I overheard a conversation that sounds as if it emanated straight from the Billy Crystal comedy, Parental Guidance. If you missed it, the film casts a humorous light on modern day, over-protective parenting practices. Not unlike the film, each child in this game received a turn at the plate each inning, regardless of the number of outs, provoking this newcomer 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.

Yet as adults, 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 blog post that celebrates failure in some way and while I agree that it can serve a higher purpose, I remain 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.

My ambivalence toward 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 observed. In the U.S., 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. They (Americans) love that story arc," Mr. Pierce said.

This is true and most recently surfaced in Business Brilliant: Surprising Lessons from the Greatest Self-Made Business Icons, written by Lewis Schiff. Mr. Schiff, the executive director of Inc. Business Owners Council, a membership organization for entrepreneurs, highlights the seven principals 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," he said in an interview with LinkedIn.

But what if not all failures can be turned into valuable life lessons? Barry Moltz, a Chicago-based author, speaker and small business consultant asserted, "Failure stinks when we are going through it and sometimes there is nothing to learn." He also observes that the business world loves to talk about great comebacks but cautions that celebrating failure is a mere 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," he said.

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, who served in the U.S. Navy. Ms. Buresh observed that 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 our newfound admiration for failure. Daniel Isenberg, a professor of management practice at Babson Global, warns against a "cult of failure," in a Harvard Business Review post, where he fears this habit is a ploy used by entrepreneurs to mitigate their anxiety.

Likewise, Art Papas, CEO of Bullhorn, a global leader in recruiting software, recently wrote in the Harvard Business Review "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," Mr. Papas observed.

So how does one 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, Texas, said she can count multiple failures but one that stands out involves a recent fumbled sales call she attended. Her "victory" came later when she asked a potential client for one more shot, went back in and won the sale.

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

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