“And So It Goes”: 5 Business Lessons from the Beautiful, Brutal, Brilliant Life of Billy Joel

“The most original thing I've ever done in my life is screw up. But that's not necessarily a bad thing. It's all in the recovery — how you correct your mistakes.” — Billy Joel, And So It Goes

I recently watched the HBO documentary Billy Joel: And So It Goes. Five hours of honesty, wreckage, redemption, and resilience. It was more than a music doc — it was a masterclass in the messiness of growth.

We see a man who became one of the most successful singer-songwriters of all time — and nearly lost everything more than once: friends, marriages, money, sobriety, confidence. Yet he kept showing up. He kept creating. He kept owning his story — even the worst parts.

As a CEO, coach, and entrepreneur, I found myself not just watching Billy Joel’s story, but feeling it. So much of what he lived through echoes what we face in business: betrayal, burnout, brilliance, and blind spots. You don’t have to be a rock star to relate.

Here are five takeaways from Billy Joel’s extraordinary, self-destructive, ultimately redemptive journey — told through a business and leadership lens.

You’re Going to Screw Up. The Question Is: Will You Own It?

Billy opens the documentary by saying:

“I’ve screwed up more than anything else I’ve done. But that’s where the good stuff comes from. It’s how you recover.”

Throughout the film, he confesses to infidelity, substance abuse, alienating friends and family, choosing the wrong people to trust (notably his ex-manager and brother-in-law who stole millions), and firing loyal collaborators when he felt trapped. As he says about the aftermath:

“I didn’t realize how much I could hurt people when I was drinking.”

In leadership, we often talk about failure in sanitized ways — “learning moments,” “pivots.” Billy reminds us that real failure has consequences. It costs trust, time, money, and relationships. But it’s in the owning of the screw-up — not the denial — that character is revealed.

Hire the Right People — But Don’t Abdicate Your Judgment

Elizabeth Weber, Billy’s first wife and manager, is described by many in the film as the person who built his career. She had instincts. She fought for him. She believed in “Just the Way You Are” when no one else did.

And then, after their breakup, Billy hired her brother, Frank Weber, as his new manager — over her warnings. Years later, he sued Frank for $90 million for embezzlement and lost nearly everything.

Business lesson? Trust is good. Oversight is better. Too often, founders hire from the gut or default to familiarity. Loyalty and chemistry are not substitutes for financial rigor, legal clarity, or operational accountability. As Billy said in the doc:

“He stole from me, and I didn’t want to believe it... I didn’t want to believe I had been that wrong.”

Creative Energy Without Structure Will Burn You Out

Billy Joel stopped writing pop songs after River of Dreams in 1993. That was over 30 years ago. Why?

“I got tired of the tyranny of the rhyme.”

He loved classical music. Pop music, for him, became a grind — not an outlet. Perfectionism crushed joy. Touring and fame became exhausting. The man who wrote “New York State of Mind” and “Scenes from an Italian Restaurant” had nothing left to say in that format.

As leaders, we often assume our top talent — or ourselves — can keep producing indefinitely. But creativity is not a faucet. Without reinvention, space, and honest self-assessment, burnout is inevitable.

Sometimes, like Billy, we need to stop doing the thing that made us successful — and start something less expected, but more sustaining.

You're Not Cool — and That’s OK

Billy was never the critics’ darling. In fact, they hated him. They called him cheesy, overwrought, sentimental, bombastic. He responded by ripping up reviews onstage.

“They hated me. And the more I let it bother me, the more they hated me.”

This is a powerful reminder: trying to be cool is the most uncool thing you can do. Whether you're running a company, launching a product, or building a personal brand — be authentic. Be excellent. Don’t chase applause from the wrong crowd.

In the end, artists like Nas, Springsteen, Paul McCartney, and Itzhak Perlman all line up to praise Billy’s songwriting. Why? Because impact outlasts approval. Joel stayed true to his melodic instincts, his love of storytelling, and his live-performance charisma. And that built a catalog that still fills stadiums.

Reinvention Doesn’t Require Reinvention — Sometimes It Just Means Showing Up Again

Toward the end of the documentary, Billy Joel sits with his daughters at the piano. He’s older. Softer. Still struggling with health issues — including normal pressure hydrocephalus, a brain condition. But he’s alive. He’s there. He’s present.

And he’s still Billy Joel.

“I still believe in love. I still believe in music. I just don’t have to prove it anymore.”

That’s a profound business insight: not everything needs to scale. Not everything needs to disrupt. Sometimes the greatest act of leadership is continuing to show up — humbled, wiser, grounded — and still finding joy in what you do.

Billy isn’t writing chart-toppers. But he is selling out Madison Square Garden. Not out of ambition, but because the songs — and the man — still resonate.

And So It Goes

There’s a moment in And So It Goes where Billy says:

“I’ve lived an extreme life. And I don’t regret it. But I’ve learned.”

That’s the real lesson. Not to avoid mistakes, but to grow through them. To love even after heartbreak. To lead after loss. To be better the next time — not perfect, but better.

That’s what business — and life — demands.

Thanks, Billy.