Learning from Billy Joel without living like Billy Joel.

On wisdom, wounds, and the stories we tell ourselves.

“Show me a hero and I’ll write you a tragedy.” ~ F. Scott Fitzgerald

When I wrote my last article about Billy Joel’s attitude of not taking any shit from anybody, I knew I’d hear from the critics. Sure enough, they arrived: “How can you hold up someone who had an affair with his best friend’s wife? What about the alcoholism? The failed marriages? The way he left collaborators behind?”

They weren’t wrong about the facts. Joel’s personal life was messy. His affair with Elizabeth Weber destroyed his friendship with Jon Small and broke up their band. His drinking was legendary and destructive. His romantic relationships were a string of public failures. By many measures, he was far from an ideal human being.

But here’s what I wasn’t asking anyone to do: handle relationships like Billy Joel, drink like Billy Joel, or treat friends like Billy Joel. I was pointing to one specific quality—his refusal to be diminished by others’ expectations or criticism, or his own doubts and fears. That attitude served him well creatively, even when his personal choices didn’t.

This is the difference between wholesale hero worship and selective wisdom gathering. We don’t need perfect people to learn valuable lessons.

Joel’s “Don’t take any shit.” mentality helped him survive music industry politics, critical dismissal of his work, and constant pressure to be something other than what he was. That resilience—that specific quality—is worth studying, regardless of how he handled his personal relationships.

When we demand moral perfection from everyone we might learn from, we eliminate most of human wisdom. Should we ignore Charles Dickens’s insights about social justice and human dignity because he made choices we wouldn’t make? Dismiss MLK, Jr.’s principles of justice and nonviolent resistance because he was imperfect in his personal life? Reject every lesson from anyone who ever hurt someone they cared about?

The alternative isn’t moral relativism or excuse-making. It’s precision. Joel’s creative tenacity: instructive. His personal relationship patterns: not so much. His artistic integrity: valuable. His drinking habits: cautionary tale.

But we also need to acknowledge that some people simply shouldn’t serve as examples of anything positive. When someone’s overall character is corrupted by cruelty, when their actions cause widespread harm, when their fundamental approach to other human beings is manipulative and destructive—selective wisdom gathering turns into dangerous rationalization. There are lines we shouldn’t cross, even in the name of extracting lessons.

The key is discernment. Joel, for all his personal failings, never built his success on the systematic exploitation of others. His flaws were largely self-destructive or hurt those closest to him—terrible enough, but different from those who weaponize their talents against the vulnerable or use their platform to spread hatred and division.

This selective approach actually makes us better judges of character, not worse ones. When we stop expecting heroes to be flawless, we start seeing people clearly—as complex beings with both strengths worth emulating and weaknesses worth avoiding.

Most importantly, it makes us more forgiving of our own contradictions. If Billy Joel could be professionally courageous while personally flawed, maybe I can work on my own resilience without waiting to become perfect first. Maybe you can, too.

The goal isn’t to become Billy Joel. It’s to learn from the life of Billy Joel.

Some readers also reached out after watching the documentary about Joel, saying they were inspired by his story but saddened by his suffering—the father who abandoned him, the financial struggles, the crushing early rejections. “If only he could have achieved the same success without all that pain,” they said.

But this reveals another layer of our complicated relationship with role models. We want their strengths without their struggles, their wisdom without their wounds. We forget an ancient parable about a farmer whose horse runs away. His neighbors lament his terrible luck. “Maybe, maybe not,” the farmer replies. The horse returns with wild mares. The neighbors celebrate his good fortune. “Maybe, maybe not.” The farmer’s son breaks his leg training the new horses. More sympathy from neighbors. “Maybe, maybe not.” Then soldiers come to draft young men for war, but spare the farmer’s injured son. Good fortune again. “Maybe, maybe not.”

What if Joel’s father hadn’t left? Would that young boy have had the freedom to develop his own musical style without the weight of his father’s classical expectations? What if those early rejections hadn’t happened? Would Joel have built the thick skin needed to ignore critics who dismissed his style as commercial or lowbrow while he was creating some of America’s most enduring songs?

We can’t know. And neither can you about your own difficult experiences.

The abandonment that breaks your heart in your twenties might teach you something that saves you in your forties. The rejection that devastates you today might be how fate connects you with something better tomorrow. The criticism that stings now might strengthen the resolve you’ll need later.

This isn’t toxic positivity or spiritual bypassing. Joel’s pain was real, and its consequences rippled through his relationships for decades. And we need to be clear: not all suffering leads to wisdom. Sometimes trauma is just trauma—destructive, senseless, leaving only scars. The father who abandons his child doesn’t automatically create a stronger artist. The betrayal that devastates someone doesn’t necessarily forge resilience. Some wounds fester rather than heal, some pain only diminishes rather than teaches.

But it’s also true that some of what we most value about his artistry—the emotional honesty, the working-class authenticity, the refusal to be polished into blandness—would not exist without those wounds. This isn’t about glorifying pain or suggesting we should seek out suffering. It’s about recognizing that the experiences that feel purely negative while we’re living them, sometimes contribute to who we become in ways we can’t predict.

We don’t get to pick the easy path to wisdom. We don’t get to skip the difficult chapters and arrive at strength. Billy Joel’s story reminds us that the very experiences we’d edit out of our own lives might be exactly what’s shaping us into who we need to become.

Maybe, maybe not.​​​​​​​​​​​​​​​​

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Stay passionate!