I didn’t expect the tears.

But there I was, sitting in a dimly lit theater, tears streaming down my face as Bob Dylan defiantly sang “Maggie’s Farm” to an audience torn between boos and cheers. I was watching A Complete Unknown with my oldest daughter, Maddie—a thoughtful Christmas gift she knew I’d treasure.

The scene that stopped me in my tracks was Dylan’s iconic performance at the 1965 Newport Folk Festival. Armed with a Fender Stratocaster, he boldly plugged in and “went electric,” breaking away from the acoustic traditions revered by the folk community. The reaction was a mix of outrage and elation. Boos echoed from the purists, but Dylan, backed by members of the Paul Butterfield Blues Band and organist Al Kooper, played on.

As a lifelong fan of the Butterfield Blues Band, seeing actors portray my music heroes—Mike Bloomfield on guitar, Sam Lay on drums, and Jerome Arnold on bass—deeply moved me. Their musicianship had always resonated with me, and witnessing their essence captured on screen added another layer of emotion to an already powerful moment.

This scene, beautifully brought to life by Timothée Chalamet as Dylan, is more than just a snapshot in music history. It’s a testament to creative courage.

Resonating with Dylan’s Defiance

I’ve watched the documentaries, taught this moment in my high school English classes, and pored over Elijah Wald’s Dylan Goes Electric. I even dedicated an episode of my Principal Liner Notes podcast to it. Yet, seeing it unfold on the big screen hit differently.

Dylan’s act of “going electric” wasn’t just about plugging in an electric guitar; it was about rejecting the status quo, staying true to his evolving vision, and embracing the risk of change. The boos, the backlash—none of it stopped him. He knew that growth required stepping out of the safe and into the bold.

That lesson transcends the 1960s. For leaders, it’s a call to innovate, to embrace challenges, and to stay true to our core values, even when met with resistance.

The Courage to Play On

As leaders, we often face our own “Newport moments.” Whether it’s introducing a new initiative, rethinking old practices, or simply challenging the comfort of the status quo, there’s always a risk of pushback. People may not immediately understand—or embrace—our vision.

During a recent faculty meeting, I introduced a new approach to teaching and learning. I’ll admit, I was nervous about how it would be received. To ground myself, I brought along my copy of Wald’s Dylan Goes Electric. On the cover was Dylan, guitar in hand, staring down the crowd with quiet resolve. That image reminded me to stay steadfast, to “play on” even when the riffs might not land perfectly with everyone. (See picture below.)

Going electric is about more than innovation. It’s about embodying the courage to grow, to inspire others, and to stay true to our vision. It’s a reminder that, as leaders, we have the responsibility to model resilience and boldness for those we serve.

A Legacy of Creative Courage

Dylan’s 1965 performance is more than a legendary moment in music—it’s a blueprint for leadership. After Newport, Dylan continued to push boundaries, recording groundbreaking albums, earning accolades, and even winning the Nobel Prize for Literature. He didn’t let the boos define him; he let his vision propel him forward.

His story inspires us to embrace creative courage. When we face the naysayers or wrestle with self-doubt, we can hold our heads high, just as Dylan did, and press forward with conviction.

Four Ways Leaders Can “Go Electric”

1. Stay True to Your Vision: Know your core values and let them guide your actions, even when facing resistance.
2. Embrace Growth: Innovation often means stepping into the unknown. Take bold steps to evolve and improve.
3. Play On Through Adversity: Be prepared for challenges. Stay resilient and committed to your vision, even when others push back.
4. Inspire Others Through Action: Your courage can empower those around you to embrace their own growth and creativity.

Dylan’s journey reminds us that leadership is not about avoiding the boos but about playing on, louder and prouder. So, let’s go electric—and inspire those we lead to do the same.

Link to my “Go Electric” episode of Principal Liner Notes