Why Barbara Corcoran Believes Kids Need to Fail Before They Can Succeed

Parents today face a paradox: the more resources we pour into our kids’ success—elite tutoring, specialized coaching, competitive activities—the less equipped they become to handle real-world challenges. Barbara Corcoran, the renowned real estate entrepreneur and Shark Tank personality, has a provocative take on this cultural trend: the best investment you can make in your kids isn’t another program or tutor. It’s letting them experience genuine failure.

The Parent Trap: When Help Becomes a Hindrance

The modern parenting playbook often reads like a rescue mission. We intervene with teachers, hire tutors at the first sign of struggle, correct homework before submission, and shout encouragement from the sidelines. The intentions are pure, but according to Corcoran, we’re producing the opposite effect.

When parents micromanage their children’s challenges, something subtle but damaging occurs: kids internalize the message that they’re incapable. They begin to believe they need external rescue. Rather than building competence, constant intervention erodes it. The child who never faces consequences learns to depend on parental bailouts. The student whose homework is always corrected never develops their own problem-solving muscles.

Corcoran observes this pattern across families and warns that it undermines the very confidence parents are trying to build. The irony is stark: we think we’re helping when we’re actually handicapping our kids for independence.

Barbara Corcoran’s Unlikely Path to Confidence: Failure and a Supportive Mother

Understanding Corcoran’s philosophy requires understanding her own childhood. Struggling with undiagnosed dyslexia, she faced genuine academic obstacles that her peers didn’t. Yet her mother didn’t fight her battles or shield her from struggle. Instead, she offered something far more valuable: belief without rescue.

Her mother repeatedly told young Barbara that she worked harder and possessed more creative imagination than those around her. But crucially, her mother didn’t solve her problems. If Corcoran failed, she faced the consequences and had to navigate them. Her mother encouraged her to focus on what she could control: her willingness to persevere, her effort level, and her creativity in finding workarounds.

That childhood lesson became foundational. Corcoran learned early that she could “out-try” anyone—that sheer determination and willingness to get back up were her true competitive advantages. Reflecting on her trajectory, she emphasizes a simple but profound truth: “getting back up is where it’s at.” It wasn’t the absence of struggle that built her confidence; it was proving to herself repeatedly that she could survive and overcome it.

This understanding now informs how Corcoran raises her own children. She’s deliberately chosen a different path than many affluent parents: she’s eschewed the endless enrichment programs in favor of something more fundamental—direct experience with consequences.

Building Real Resilience: How Work Experience Shapes Character

Corcoran has pushed both her kids toward summer employment—not because they need money, but because they need the character-building experience that only work provides. Her son took on a grueling position making cold calls for eight hours daily, a job designed to build thick skin and persist through rejection. Her daughter worked cleaning dog kennels and walking dogs for $10 an hour—honest, physically demanding labor with countless opportunities to face small failures and frustrations.

These weren’t resume-building opportunities or networking positions. They were deliberate crucibles for developing resilience and work ethic. When her daughter eventually earned a $2.50 hourly raise, the pride she felt was transformative. She had earned it through consistent effort and demonstrated value. That’s fundamentally different from a parent praising effort or teachers awarding participation trophies.

Corcoran contrasts this approach with the typical parental path: day camps, tutoring intensives, enrichment programs. She insists that early work experience—with all its awkwardness, challenges, and occasional humiliation—teaches more about navigating the real world than traditional education ever could. Kids who work learn to manage different personalities, handle criticism, persist through tedium, and understand the relationship between effort and reward.

From Paychecks to Pride: Teaching Financial Independence

That $2.50 raise represented something beyond monetary value—it symbolized the beginning of genuine financial agency. Corcoran’s daughter saved her earnings toward a larger goal: buying a car. For the first time, she viscerally understood how hard it is to earn money and what that meant for spending it wisely.

This experience inoculates kids against entitlement. Children who’ve never had to earn struggle to respect money or understand resource constraints. Those raised in financial privilege without earning context often become adults who take prosperity for granted. Corcoran deliberately chose to keep her kids grounded by making them earn—not out of necessity, but out of necessity for character.

Kids who learn this lesson early develop a healthy skepticism toward easy gains and a respect for genuine accomplishment. They’re better positioned for the workforce because they’ve already experienced managing different personalities, handling setbacks, and persisting through unglamorous tasks. They understand that confidence isn’t inherited; it’s earned through repeated small victories.

Corcoran makes a bold comparison: “Getting a kid a job early on, versus another day camp or something, is more important than education in the schoolhouse, which parents are very willing to spend a ton of money on.” She’s not dismissing traditional education but rather highlighting what schools simply cannot teach: the character-building benefits of working within constraints, earning your keep, and managing real consequences.

The Paradox of Modern Parenting

Barbara Corcoran’s approach challenges a fundamental assumption of contemporary parenting: that more resources, more intervention, and more protection equal better outcomes. Instead, she argues for a counterintuitive truth—that some of the most valuable lessons come not from what we provide, but from what we allow our kids to experience, navigate, and overcome on their own. The kids who learn to fail early become the adults who succeed persistently.