THE BLOG
01/05/2015 05:57 pm ET Updated Mar 07, 2015

Are Millennials Too Big to Fail? Why Self-Esteem Is Blocking Our Kids From Success

Quick -- who's more likely to form a start-up company this year? Your neighbor's 24-year-old kid with a knack for apps, or the recently retired public-school teacher down the block?

If you were sure it was the 24-year-old, you'd probably be wrong. According to a recent Wall Street Journal analysis, startups by 20-somethings are at their lowest in 24 years, from 10.6 percent in 1989 when the Feds started collecting the data, to 3.6 percent in 2013.

It would seem that the population most suited to risk-taking -- young and healthy 20-somethings, unaccountable to spouses or children or mortgages and relatively debt-free except student loans -- are actually the lowest risk-takers. According to the Kaufman Foundation, which studies small-business trends, the largest-growing group of entrepreneurs is aged 50-plus. Millennials barely show up on the radar. So what gives?

Millennials, as 18-34-year-olds are known by demographers, have been called, by some, the most cossetted generation in history. Raised by helicopter parents for whom the phrase "self-esteem" often was more important than discipline or hard work, millennials were told from birth that they, like Bank of America, were simply too big to fail. So it is any surprise that so many of them are too risk-averse to start a business, where they might be faced with such an alien notion as failure?

Egged on by parents, teachers, coaches, and a multitude of parenting "experts," today's 20-somethings were raised to believe that they were, indeed, the center of the universe. If they got a bad grade, the test must have been too hard. If they didn't show up regularly to soccer practice, they still got to play because their feelings might get hurt. If they came down to breakfast with their pants on backwards, they got a big "Yay!" because after all, they dressed themselves, didn't they?

I still remember a particular math test my daughter failed in 5th grade. Always a bright student but with consistent low grades, she didn't study for it, nor was she in the habit of regularly doing her homework, so it wasn't a surprise for me to see a 59 percent at the top of the test the next day. I was surprised, though, at the teacher's comment next to it: "Good job!"

I figured I must have made a mistake, that maybe the scoring was out of 60, or 70, or even 80, so I asked my daughter if the 59 was out of 100 points. "Yes," she replied, with a shoulder shrug.

"Do you understand why you failed the test?" I gently asked, sure that now, finally, she would comprehend the cause and effect of not studying the material, and vow to study harder next time. How naïve of me.

"But I didn't fail, Mommy. See? It says right here, good job!"

And the exclamation mark was dotted with a smiley face.

Ten years of relentless parenting, 10 years of teaching my child that actions have consequences, that the surest way to academic or any other success was to study hard and put in the work, all down the drain in the five seconds it took the teacher to turn an exclamation point into a smiley face. In happy, purple ink, no less.

I called the teacher the next day, and tried, in as non-confrontational manner as I could muster, to explain why it was important for my daughter to understand that she failed, why she failed, and to feel some of the pain of failing. I explained to this very sweet 25-year-old education major, as kindly and gently as I could, that failing was an essential part of learning, and only by actually feeling the failure, preferably in this case via a glaring red, circled "F," would my daughter get stronger, take her studies more seriously, and go on to succeed the next time.

The teacher looked at me like I had three heads. I'm also pretty sure she was contemplating a phone call about me to social services.

In turn, she explained to me how much more important it was to not hurt a child's feelings, to encourage her self-esteem by turning a negative (59) into a positive (good job!). She sagely assured me that she had vigorously studied the effects of positive reinforcement on young students and was sure my daughter would do better on the next test, as result.

And it's true, my daughter didn't fail any more math tests that year. But she also never truly studied hard for another test again. She ended that year with a 70 average, but so what? Look at all that self-esteem!

I've repeatedly tried, in the eight years since that episode, to reinforce the idea that she could bring up her grades if she would just study harder, and that her feelings of self-esteem would be a hundred times greater when she actually earned it. But in her mind, and I know in many others, she never really failed, so she doesn't have to push harder. She and many of her peers now have the self-esteem of giants. Too bad they don't have many of the accomplishments to go with it.

Too important to fail. According to a Babson College survey, over 41 percent of 20-somethings named "fear of failure" as the biggest roadblock to starting their own businesses. The generation that should have been the beacon of trail-blazing, innovation, and sheer grit is, in reality... chicken. They've never actually failed at anything, so why start now?

And who can blame them? The parenting experts and educrats of recent years replaced merit and hard work with "feeling good." Equal opportunity for all has turned into a policy of forced, equal outcomes for all, regardless of input or skill. Students who can't read or write at grade level are regularly pushed into the next grade so they won't feel stigmatized at being left behind, resulting in the highest number of remedial courses for incoming college freshman in history. Nobody fails, and everybody gets a medal.

We have parents so obsessed with their child getting into the "right" college that they're writing their application essay for them, or subcontracting them out for very high fees. During middle school, a low grade means a visit by the parent to the teacher, not to demand red ink over purple but to complain that Johnny deserves a higher grade because the teacher made the test too hard. Johnny's crucial self-esteem is so much more important than Johnny actually understanding the Pythagorean Theorem.

Never mind that Johnny wants to be an architect and will have to know something about geometry, at least he'll feel good about himself. Except... he probably won't.

Twenty five percent of post-college millennials still live with their parents two years after graduating. It's fair to blame a bad economy, and many of them are working while saving on rent. But some of these live-at-home grads are also turning jobs down, either because they feel over-qualified for what used to be called entry-level positions, or are so scared at the thought of rejection, of failing, that they're waiting for the jobs to come to them.

Hopefully, a good number of them will take the plunge, anyway, either by starting at the bottom somewhere and working their way up, or starting their own business, possibly failing, and getting right back up again, better than they were before.

I actually have faith in these millennials, if for no other reason than my parents were probably saying the same thing about my generation, and previous generations before us, and here we all are, innovating and moving forward still.

It's never too late to learn how to fail, as long as they remember the ultimate lesson of failing -- fail fast and big, so you have plenty of experience and energy to overcome the later hurdles, and succeed.