The inner Wrecking Ball

The night John Lennon's self-doubt wounded Carole King—and what it teaches us about the hidden damage we do when we feel like frauds

When Our Inner Critic Becomes a Wrecking Ball: How Imposter Syndrome Hurts More Than Just You

Picture a smoky New York party in the 1960s. The room's buzzing with the era's hottest songwriters and musicians, martinis in hand, everyone trying to look cooler than they feel. In one corner, you've got Carole King—the woman who wrote "Will You Love Me Tomorrow" and basically soundtracked half of America's teenage years. Across the room, John Lennon, riding the early wave of Beatlemania and probably feeling like he needs to prove he belongs in this room full of established talent.

What happened next was one of those moments that seems small but leaves a scar that never quite heals.

During a conversation about music and politics, King shared her thoughts about the emotional weight artists carry when their work becomes bigger than themselves. Lennon's response? A cutting remark that essentially dismissed her entire body of work as shallow pop about teenage heartbreak. The room went quiet. King quietly excused herself, stunned.

Years later, she'd describe it as encountering "brilliance and cruelty at once." But here's what makes this story so important for entrepreneurs and anyone building something meaningful: Lennon wasn't being cruel because he was a bad person. He was being cruel because he felt like a fraud.

The Fraud Inside the Icon

Here's something most people don't know about John Lennon: despite being in the most successful band in history, he was constantly battling feelings of inadequacy. He once said, "Part of me suspects that I'm a loser and the other part of me thinks I'm God Almighty." Sound familiar?

That internal ping-pong match between "I'm amazing" and "I'm a total fake" is imposter syndrome in its purest form. And it affects over 80% of us at some point—including people who, from the outside, look like they have it all figured out.

But here's the part nobody talks about: when we feel like frauds, we often try to make others feel smaller. It's like we think there's only so much "legitimate success" to go around, so if we can poke holes in someone else's achievements, maybe ours will seem more real.

Lennon's attack on King wasn't really about her music—it was about his own terror that he didn't deserve to be in that room. The problem? King was dealing with her own version of the same struggle. She'd written hit after hit, but she still questioned whether she belonged among the "rock elite." His words didn't just sting in the moment; they confirmed her worst fears about herself.

The Ripple Effect Nobody Sees

When our imposter syndrome turns us into critics and competitors instead of collaborators, the damage spreads in ways we never intended:

It plants seeds of doubt in others: King spent months questioning her worth after that encounter. One comment from someone she respected professionally undid what years of chart success should have solidified. Think about that—months of self-doubt from a few seconds of someone else's insecurity.

It reinforces the worst parts of our industries: That party took place in the 1960s, when women in music already had to fight twice as hard for half the recognition. Lennon's comment didn't exist in a vacuum—it fed into a culture that was already telling King she didn't quite belong.

It destroys potential partnerships: Two brilliant songwriters, both struggling with self-doubt, could have found common ground and mutual support. Instead, fear created a wall where a bridge might have been built.

It creates lasting wounds: King talked about this incident decades later. The words we throw around when we're feeling insecure can echo in someone's head for years, influencing decisions and self-perception long after we've forgotten we even said them.

Your Boardroom, Same Story

This isn't just about 1960s music parties—this plays out every day in modern business. I've seen it in countless networking events, team meetings, and industry conferences. When entrepreneurs feel like imposters (which, let's be honest, is most of us most of the time), we often:

Downplay others' wins to make our own look bigger. "Oh, they just got lucky with timing" or "That's not really that innovative."

Become the critic instead of the cheerleader. We find flaws in competitors' products, poke holes in peers' strategies, anything to feel like we're the ones who "really get it."

Pull back from collaboration because we're terrified someone will discover we don't know what we're doing.

Create teams that walk on eggshells because our own insecurity makes us hypercritical of everyone around us.

I've watched brilliant entrepreneurs sabotage potential partnerships because they were too afraid of looking stupid. I've seen startup founders tear down their competition instead of focusing on building something great. And I've been guilty of it myself—those moments when someone else's success makes you feel smaller, so you find reasons why it "doesn't count."

Breaking the Cycle (Before You Break Others)

The good news? Once you recognize this pattern, you can change it. Here's what I've learned from my own journey and from watching other entrepreneurs work through this:

Catch yourself in the moment. Before you speak, especially when you're feeling triggered or insecure, ask yourself: "Am I about to say this because it's true and helpful, or because I'm feeling threatened?"

Flip the script on success. Instead of seeing someone else's achievement as proof you're not good enough, try seeing it as proof that good things are possible in your industry. Their win doesn't use up your win.

Get comfortable with not knowing everything. The entrepreneurs who last are the ones who can say "I don't know" without feeling like frauds. Turns out, nobody expects you to have all the answers—they just want to know you're honest about what you don't know.

Find your people. King spent that party alone in a corner, processing the hit. But imagine if she'd had a friend there who could say, "That guy's just intimidated by your talent." Having people who remind you of your worth when you forget makes all the difference.

The Grace to Grow

Here's what I love about King's eventual response to that whole mess: she didn't turn Lennon into a villain. Years later, she said, "I don't think he meant to wound. But he did." That's the mark of someone who's done the work—she could acknowledge the harm without demonizing the person who caused it.

That's the kind of leader I want to be, and probably the kind you want to be too. Someone who feels the imposter syndrome (because we all do) but doesn't let it turn us into weapons against other people trying to build something meaningful.

The Better Party

Sometimes I think about how that party could have gone differently. What if Lennon, feeling his insecurities spike as King talked about artistic integrity, had said something like, "Man, I struggle with that too. How do you stay authentic when everyone's watching your every move?"

What conversations might have happened? What songs might have been written? What mutual support might have developed between two artists dealing with the same fears in different ways?

We can't rewrite that night, but we can write our own nights differently. The next time you're in a room where you feel like you don't belong—whether it's a networking event, a board meeting, or just a conversation with someone whose success makes you feel small—you have a choice.

You can be the person who builds others up, knowing that in a world full of talented people wondering if they're good enough, a little genuine encouragement might be the rarest gift you can give.

Because here's the thing: whether you're writing songs or building software, the best harmonies happen when everyone's trying to make the whole thing sound better, not when they're all fighting to be the loudest voice in the room.

Your imposter syndrome is real, and it's valid. But it doesn't have to become someone else's soundtrack of self-doubt.

Photos: John Lennon; UK Govt; Public Domain Carole King; Cash Box Magazine; Public Domain