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Redefining Success Through Stoic Wisdom

“What would the Stoics think about how we measure success?”

It’s a question I’ve often asked myself — especially in a world where metrics are driven by followers, likes, bank accounts, and headlines. But one of my favorite quotes from Marcus Aurelius grounds me every time: “Very little is needed to make a happy life; it is all within yourself, in your way of thinking.”

That’s the foundation for this conversation with someone I deeply admire professionally and personally.

Dr. Chuck Chakrapani has been a mentor, a friend, and a source of unshakable clarity in my life for over 25 years. Our relationship has been built over long walks, shared meals, and the kind of deep, introspective conversations that linger in your mind for decades. From his roles as President of Leisure Analytics and CEO of Millward Brown Canada to his extensive work in legal IP cases as a leading expert witness, Chuck has built a professional legacy that spans industries and borders. He’s been editor-in-chief of industry-defining magazines, authored numerous books, is a Fellow of both the Canadian Research Insights Council and the Royal Statistical Society, and currently serves as Chief Knowledge Officer at Blackstone Group. Oh—and in his “free” time, he’s a day trader and a Distinguished Visiting Professor at Toronto Metropolitan University’s Ted Rogers School of Management.

Yet it’s in this next evolution of his life — as an author and advocate of Stoic philosophy — where Chuck has made, perhaps, his most profound impact.

During our conversation, I asked Chuck a simple but revealing question: “What does success look like to you?” His answer wasn’t a list of accolades or achievements but a reflection on a moment that changed the course of his life. It was his grandmother, questioning the frantic pace of his life and the empty reward of external validation. That voice stayed with him. And years later, when Chuck had achieved what most would consider the pinnacle of success, he realized he still wasn’t at peace. He was still rushing. Still not present. That’s when the real shift happened.

He began to define success from the inside out—not by what others expected of him, but by what truly mattered to him: time with friends, good meals, space to think, freedom from external validation. As he put it so beautifully, “Success is whatever you do from inside out.”

That is a radical idea in today’s business culture. But it’s also deeply Stoic. Stoicism teaches that true freedom comes from within—specifically, from focusing only on what is within our control, and releasing the rest.

When I asked Chuck about one of the hardest lessons he’s learned along the way, he didn’t hesitate. “You have to learn to be independent of other people’s opinions.” That statement landed deeply with me. As leaders, we are constantly surrounded by voices telling us what we should do, how we should be, and what should matter. But there is profound power in freeing ourselves from that external noise. Chuck admits it’s a lifelong lesson; one he’s still learning. “I worry about what you’ll think of me,” he laughed, “what the audience will think.” That humility, that openness to continued growth, is part of what makes Chuck’s leadership so extraordinary.

It’s also part of why his embrace of Stoicism is so meaningful. When asked to explain it simply, he laid it out with characteristic clarity: “We spend most of our time worrying about things we can’t control—and very little time acting on what we can.” That’s the Stoic paradox. And that’s the mental model Chuck lives by. It’s changed my life. Truly. As a leader, as a human being, as a mission-driven business builder – it has helped me stay grounded in what matters.

What struck me most in our conversation was Chuck’s response to the idea of disruption. So many of the executives I speak to talk about “disrupting markets” or “leading transformation.” But Chuck’s approach is different. He simply asks: What needs doing here? That quiet clarity guides every role he steps into. He doesn’t aim to disrupt. He aims to serve — effectively and purposefully. And ironically, that often is the disruption. Because in a world obsessed with noise and scale, calm, deliberate action rooted in internal alignment is revolutionary.

That mindset isn’t just admirable, it’s actionable. Imagine if every leader paused and asked: What needs doing here? Imagine how many more mission-driven, human-centered decisions we would make.

And in true Stoic fashion, when we asked Chuck what we could do for him, he said, “I don’t need anything.” That, to me, is the truest measure of success — not needing anything because you’ve already built a life aligned with your values, your priorities, your joy.

So, to everyone reading this—take a page from Chuck’s book (literally, if you haven’t read Stoicism, Cobwebs, and Gems yet, it’s a must!). Redefine success on your own terms. Measure it by the quality of your thoughts, not the weight of your resume. Build it from the inside out.

Because very little is needed for a happy life.

And it all begins within.

If you want to learn more, watch the full interview on C-Suite TV or download the podcast on C-Suite Radio or wherever you listen to podcasts.

Tricia Benn
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