We caught up with the brilliant and insightful Cordell Winter a few weeks ago and have shared our conversation below.

Hi Cordell, thanks for joining us today. We’d love to hear the backstory behind a risk you’ve taken – whether big or small, walk us through what it was like and how it ultimately turned out.

My entire life has been a risk.

Whether it was living in a van, traveling to another country in search of a booking agency, sleeping in a car for a month while I was there, staying on random couches with people I had just met in the streets as they drove deep into a foreign wilderness, jumping off waterfalls in Tennessee many feet high without knowing how deep the water was, or—regarding your question—choosing a music career over a conventional life.

For me, even those actions were never simply about recklessness. They were a pursuit of poetry—a search for notes and lines from the ledges of the human spirit, a willingness to push into the unknown.

I have always carried an inseparable calling to want to help people awaken their lives. Obsessive in a way.

Music became that vessel.

The risks of chasing a career in music before seeing a rise in success have been homelessness, losing romantic relationships, sacrificing stability, walking away from financial security, and chasing an outcome that offers no guarantee of ever playing Madison Square Garden one day or having a safe life.

There have been many risks in my story I took to accomplish my dreams, one that comes to mind was recording my first album. At Universal House of Blues Studios in Berry Hill lived in my van in 40 degree weather in the winter and decided to camp outside the studio until they finally agreed to record me. I ended up living in that studio for a few years and was even given the key to the place haha!

There have been moments when I sat in the private recording studios of well-known artists, listening as they told me my songs weren’t good enough, only to watch them later collapse drunk and high while I sat there hoping for their acceptance. Years later, those same songs carried me across Europe and the U.K., to stages like the Sturgis Buffalo Chip and other festivals, allowing me to play music around the world. More importantly, they helped me earn the respect I was searching for all along.

There is risk in every tour—the battle to sell tickets, the pressure to make every show work, the responsibility of keeping the machine moving. There is risk every year in meeting expectations and continuing to compete in an industry that offers no guarantees.

But I believe all of those risks matter.

I believe they will become proof for some young kid one day that’s contemplating his dreams that a life can exist beyond conformity—that whatever voice calls an individual toward their purpose is worth listening to.

For me, that kind of freedom has value. Whether in this life or beyond it, I believe it is something worth living for.

Cordell, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?

An Article written on Musician/ Poet
Cordell Winter – Written by: Lauren Leitner

The Man Who Refused the Cage: The Unsung Story of Cordell Winter

History tends to celebrate those who build empires, accumulate wealth, and leave monuments behind. It rarely remembers those who spend their lives asking a far more dangerous question:

“What if none of this is really freedom?”

In this story, there is a man named Cordell Winter who challenged everyone around him to consider that possibility.

To some, he was reckless. To others, irresponsible. Yet to the people whose lives he touched, Cordell represented something increasingly rare in the modern world: a person willing to live exactly as he believed.

He rejected the conventional path laid before him. Status, careers, possessions, and social expectations held little interest. Instead, he devoted himself to experience—to chasing music, poetry and adventure across oceans, living in the present, and searching for moments that made him feel undeniably alive.

What made Cordell remarkable wasn’t his love of adventure. Many people seek thrills. What set him apart was his refusal to separate his philosophy from his actions. He didn’t merely talk about freedom; he organized his entire existence around it.

Those who knew him describe a magnetic figure. He possessed the unusual ability to make strangers question the assumptions governing their own lives. In his presence, ordinary routines suddenly seemed less certain. The endless pursuit of more money, more approval, and more security appeared less convincing.

Cordell believed fear was the greatest prison ever created. Fear of failure. Fear of judgment. Fear of stepping beyond the boundaries society draws around acceptable lives.

His answer was simple: confront it.

Whether standing before the music industry or difficult truths, he encouraged others to discover what remained after fear had been stripped away.

Critics argued that his philosophy was naïve. Perhaps it was. Freedom has always appeared dangerous to those who value control. Yet even his critics acknowledged that Winter possessed something many successful people spend entire lifetimes searching for: authenticity.

He was not trying to become someone. He already was.

In an age increasingly defined by distraction, consumption, and conformity, Winter’s greatest contribution may have been reminding people that life is not measured by what we own but by what we experience.

He left questions.

What does it mean to truly live?

How much of our lives are shaped by expectations we never chose?

And what would we become if we were brave enough to let go?

The world may never place Winter among its celebrated heroes. Yet for countless dreamers, wanderers, artists, and seekers who have felt confined by invisible walls, his message continues to echo:

The biggest risk is not losing everything.

The biggest risk is never discovering who you are beyond the cage.

We’d love to hear a story of resilience from your journey.

Around the COVID era, years of work fell through. Between the pressure, carrying an entire business on my shoulders, loyalty of band members and navigating a lot of industry disappointments and false promises. I found myself in a very dark chapter of my life.

That season sent me out West to reconnect with the earth in a way that completely redefined my journey and reaffirmed that I was on the right path.

When I returned to Nashville Tennessee, I independently took my own path, After relentlessly hitting the road on tour I was given the opportunity to play the Sturgis Buffalo Chip, one of the biggest festivals in the United States. Seeing my name on the lineup shirt alongside artists like Jelly Roll was a moment I’ll never forget.

I’ve always imagined it must have felt somewhat like Blind Melon had felt stepping onto the stage for their biggest performance at Woodstock ‘94 or Sublime experiencing those breakthrough moments before Bradley Nowell’s passing—a feeling that years of belief, sacrifice, and persistence had led somewhere meaningful.

What makes that moment even more significant to me is everything that came before it. The year prior, on my journey home and visions through the Black Hills and the deserts, I experienced things that felt truly ineffable—otherworldly moments that are difficult to put into words. Those experiences stayed with me. Looking back, it feels as though God were preparing me for what was ahead.

That festival wasn’t just another show. It felt like a confirmation that I was exactly where I was supposed to be and it really propelled my career. It’s a moment that will stand the test of time for me.

Learning and unlearning are both critical parts of growth – can you share a story of a time when you had to unlearn a lesson?

The idea that anything great comes on your time—or that dreams have an expiration date—is something I’ve struggled with. I think the best at any craft spend their entire lives studying and refining their work, chasing its highest peak of knowledge. For a long time, I was fixated on the idea that it had to happen by a certain age or at a specific moment. Over time, I’ve realized I’ll be doing this regardless of what it brings, simply because it’s part of who I am. Whatever comes from it is a bonus. I still have to remind myself of that sometimes, haha.

Contact Info:

• Website: https://www.cordellwinter.com/
• Instagram: https://www.instagram.com/cordellwinter/
• Facebook: https://www.facebook.com/CordellWinterOfficial/
• Twitter: https://x.com/CordellWinter
• Youtube: https://youtube.com/@cordellwinter?si=FNs_WDVxIyUNNjZ0
• Other: https://linktr.ee/CordellWinter

Image Credits

Matt Workman Videography