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From Adversity to Altitude — Redefining Success on Your Own Terms

What defines success?

It’s a question we all face at some point, and if we’re lucky, we get to redefine it on our own terms. On this episode of C-Suite Success, I had the great honor of speaking with someone who has done exactly that—and helped countless others along the way: James W. Keyes. Or, as I know him, Jim.

Jim is the former CEO of not one but two iconic Fortune 500 companies—7-Eleven and Blockbuster. He’s a bestselling author, philanthropist, commercial pilot, artist, and a true modern-day Renaissance man. Whether he’s shaping the future of education, serving on the boards of elite institutions, or flying high (literally), Jim’s life is a masterclass in leadership, service, and possibility.

When Jim joined me for this conversation, I asked him to define what success meant for him. His answer was as insightful as it was personal. He recounted a transformative moment: walking across the campus at Columbia University—years after attending graduate school there—and seeing a student wearing a T-shirt that read: “Education is Freedom.”

That moment became the seed for his book Education Is Freedom: The Future Is in Your Hands, and a turning point in his own understanding of success. “It stopped me in my tracks,” Jim said. “I realized I had thought it was all about the money. I was wrong. It’s about freedom—the freedom to learn, to grow, to chart your own path.”

That freedom, as Jim powerfully shared, doesn’t come from a paycheck—it comes from knowledge. “I learned how to learn,” he said, “and that means I can pivot, evolve, and do anything.”

It’s no accident that Jim became a pilot. “The sky’s no longer the limit,” he told me. “It’s just the beginning.” But what he said next struck even deeper: he sees every opportunity to learn not as a checkbox, but as a responsibility. “Even as a pilot, every year I go through intensive training. They lock me in a simulator for three days and try to kill me,” he joked. “Because learning is ongoing. To lead, you must continue learning. It’s a license to learn—not a finish line.”

We spoke about success not as a destination, but a journey of resilience—one that, in Jim’s case, began long before the boardroom. From a turbulent childhood marked by instability and adversity, Jim developed the grit and perseverance that would later serve him through some of the biggest corporate storms in modern history.

Jim didn’t just lead companies—he led them through crisis. At 7-Eleven, he joined just before the 1987 market crash. At Blockbuster, it was the 2008 financial meltdown. But what many would call setbacks, Jim saw as fuel. “My childhood prepared me for this,” he said. “I had no safety net. So I learned to ask: ‘How do I figure this out?’”

When 7-Eleven filed for bankruptcy, Jim leaned in. “Everyone around me had their heads down, but I chose to see the opportunity. We had to reinvent ourselves.” That mindset didn’t just lead to a turnaround for the company—it earned Jim a promotion and set the stage for the strategic vision he’s known for today.

As we talked, it became clear that Jim’s view of leadership is deeply rooted in this idea of transformation through change. In his words: “Change equals opportunity.” That’s not just a mantra—it’s the title of a chapter in his book, and the throughline of his career. He’s the kind of leader who runs toward disruption, not away from it.

But what makes Jim so exceptional—beyond the accolades and board seats—is his heart. He’s a passionate advocate for education, equity, and community. From founding the Education Is Freedom Foundation to serving on the boards of the American Red Cross, Dallas Symphony Orchestra, and Columbia Business School, Jim continues to give back with purpose and impact.

I asked Jim what it was like to be a man who wasn’t expected to “do even a tenth” of what he’s accomplished—and his answer was disarming in its humility. “One one-thousandth, maybe,” he smiled. And yet, with every barrier he’s broken, he’s created a pathway for others.

Our conversation was a powerful reminder: success is not about titles, trophies, or tenures. It’s about who you become in the process—and who you lift up along the way.

Jim Keyes is a walking testament to that truth.

So, here’s the takeaway for all of us in the C-Suite community and beyond: define your own success. Own your freedom. Keep learning. Embrace change. And when the world hands you turbulence, find the opportunity to fly higher.

Watch the full interview on C-Suite TV or listen to the podcast on C-Suite Radio (or wherever you listen to podcasts).

Tricia Benn
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