Leadership Lessons from Billy Joel's Historic Madison Square Garden Residency

Billy Joel’s historic residency at Madison Square Garden, spanning January 2014 to July 2024, was a cultural milestone, with 104 performances and only a brief pause during the COVID shutdown. Living just 45 minutes from New York City in New Jersey, I hadn’t taken my family to see him perform. That changed during the pandemic when I heard on Q104.3, my favorite classic rock station, that Billy Joel’s concerts would soon resume, and tickets were about to go on sale.

My wife and I had seen Billy Joel several times, but never at Madison Square Garden, his true home stage, and never with our teenage kids. I wanted them to experience the magic of live music from legends like Billy Joel and Elton John before they retired from touring. When tickets went on sale, I secured four for a show seven months out, thrilled to finally bring my family to see him.

Days later, Q104.3 announced a contest: “Billy’s Biggest Fan.” The prize? Tickets to see Billy Joel at Madison Square Garden every month for six months. To enter, you needed to submit a short essay explaining why you were his biggest fan. The odds seemed daunting—millions in the tri-state area listen to Q104.3, and Billy Joel is a universal favorite. Most would dismiss it as a long shot, like winning the lottery.

But a lesson from my son’s high school hockey team came to mind. A few years earlier, the team offered a $1,000 college grant for the best essay about lessons learned during the season. With only 20 players, the odds were great, but when my wife and I attended the awards ceremony, we learned no one had submitted an essay. The coach explained that every player assumed they wouldn’t win, so they didn’t try. A single sentence could have claimed the prize.

That memory fueled my resolve. I wasn’t going to let slim odds stop me. Inspiration struck from my daughter, an old soul with a knack for curating incredible music playlists. A few weeks earlier, I noticed one on her phone titled “Who is Elton John?” She explained that her friends, unfamiliar with classic rock, would ask about her music. When she played Elton John, they’d say, “Who’s this?” She’d reply, “Elton John!”—and they’d ask again, “Who is Elton John?” Amused, she named her playlist after their question.

I crafted a concise essay for the contest, adapting her story. I wrote about my 15-year-old daughter’s playlist, “Who is Billy Joel?” and how she introduced her friends to classic rock, choosing Billy Joel, the Rolling Stones, and Elton John over mainstream pop like Taylor Swift. It was a simple, heartfelt pitch.

Weeks later, my phone rang. It was Jim Kerr from Q104.3, asking to read my essay live on air. I had won! With the six months of contest tickets plus the four I’d already bought, my family had seven months of Billy Joel performances to enjoy.

The Leadership Lesson

“Whether you think you can, or you think you can’t—you’re right.” – Henry Ford

This experience taught me a powerful leadership lesson. I set a goal, drew inspiration from my kids, and believed winning was possible despite the odds. Instead of making excuses or assuming failure, I took action. I wrote the essay. I made the effort. Like doing one more push-up, that small act of persistence made all the difference.

Disclaimer:  This post is mine alone and may not be the views or opinions of any others, including past or current employers, friends, or family.  You can also find me on Substack, Medium, Tumblr, Facebook, LinkedIn, and X – and you can find my book here on Amazon