After interviewing some of the world’s most accomplished entrepreneurs, business leaders, and cultural icons, I discovered that the most revealing answers rarely had anything to do with money. One simple question often told me more about a person than their entire professional biography.
Throughout my career as a journalist and Editor-in-Chief, I’ve had the privilege of sitting across from some extraordinary people. Billionaires, entrepreneurs, bestselling authors, professional athletes, entertainers, and business leaders whose names have become synonymous with achievement.
I’ve interviewed people who have built companies worth millions, transformed industries, influenced entire generations, and accomplished things most of us can only imagine. Their professional biographies were impressive, their schedules were demanding, and their stories often began long before the world knew their names.
But during my years behind the editor’s desk at SUCCESS® magazine, there was one question I loved asking almost everyone I interviewed.
“What is your definition of success?”
It sounds simple, doesn’t it? Perhaps even a little predictable for a magazine called SUCCESS. But I found that the answers were often anything but.
You see, I wasn’t particularly interested in hearing another list of accomplishments. By the time someone reached the point of being considered for a major feature or cover story, I already knew what they’d achieved. I’d done my research, reviewed their background, and understood the professional milestones that had brought them to that moment.
What I wanted to understand was the person behind those achievements.
What did success mean to them? Had that definition changed over time? And after reaching levels of wealth, recognition, and influence that so many people spend their lives pursuing, what did they believe really mattered?
Those conversations taught me something I continue to carry into my work with entrepreneurs and leaders today. The most interesting part of someone’s story isn’t always what they’ve accomplished. It’s what those accomplishments have taught them about themselves.
When Success Becomes Something Bigger Than Yourself
I remember interviewing Daymond John, the entrepreneur, investor, and familiar face from Shark Tank.
Here was someone who had built an extraordinary business career, created a globally recognized brand, and become a respected voice in entrepreneurship. By almost any conventional measure, Daymond had achieved tremendous success.
But when I asked him what success meant to him, his answer went beyond financial achievement.
He spoke about the inner knowing that you’ve made an impact on something bigger than yourself.
That stayed with me.
Because when you think about it, there’s something incredibly powerful about reaching a point in your life when success is no longer defined solely by what you’ve accumulated, but by what you’ve contributed.
For someone who has spent years building businesses, creating opportunities, and influencing others, that shift in perspective says a great deal.
It also raises an interesting question for those of us still working toward our next professional milestone: Are we building something simply to prove that we can, or are we building something that will matter beyond ourselves?
I think there’s room for both ambition and contribution. In fact, some of the most meaningful careers I’ve witnessed have been built on the relationship between the two.
But I’ve also learned that the satisfaction we imagine will come from reaching a certain level of success doesn’t always arrive in the way we expect.
Sometimes the achievement is just the beginning of a much more interesting conversation.
What Tony Robbins Taught Me About Mindset
Another conversation that stands out was with Tony Robbins.
Tony has spent decades helping people rethink their beliefs, challenge their limitations, and approach their lives with greater intention. He’s built an extraordinary career around understanding human behavior, performance, and personal transformation.
When we discussed success, his perspective came back to something that has been central to his work for years: mindset matters most.
And I understood why.
You can have the opportunities, the resources, the connections, and the credentials, but the way you think about yourself and your circumstances influences what you do with them.
I’ve seen that play out countless times throughout my own career.
Some of the most accomplished people I’ve interviewed have faced extraordinary setbacks. They’ve lost businesses, experienced personal hardships, made decisions they regretted, or found themselves having to rebuild when the world assumed they already had everything figured out.
What interested me wasn’t simply how they recovered. It was how they interpreted those experiences and what they chose to believe about what came next.
Tony’s emphasis on mindset reinforced something I had observed through years of interviewing successful people: achievement is only one part of the equation. The way you experience your life, respond to adversity, and understand your own potential is equally important.
And that perspective becomes particularly relevant when you’re leading a company, managing a team, or navigating the uncertainty that comes with entrepreneurship.
The Answers That Didn’t Appear on Their Resumes
One of the things I loved most about my work at SUCCESS was the opportunity to move beyond the familiar narratives surrounding high-profile individuals.
By the time I interviewed someone, there were often dozens, sometimes hundreds, of articles already written about them. Their business achievements were well documented. Their public image had been carefully established. Their teams knew which stories they wanted to tell.
But I wasn’t interested in simply repeating what readers could find elsewhere.
I wanted to understand what made them human.
And asking someone to define success often created an opening for a different kind of conversation.
It invited reflection rather than promotion.
Instead of telling me what they’d done, they had to consider what it meant.
Sometimes the answer involved family. Sometimes it was freedom, peace of mind, personal growth, or the ability to create opportunities for others. Other times, it revealed how dramatically someone’s priorities had changed since the early days of their career.
I found those moments fascinating because they reminded me that even the most recognizable people are still navigating many of the same questions we all face.
Am I doing work that matters? Am I making the right decisions? Have I sacrificed too much along the way? What do I want the next chapter of my life to look like?
The size of someone’s bank account doesn’t eliminate those questions.
If anything, achieving extraordinary success can make them even more important.
Why I Believe Every Entrepreneur Should Know Their Own Answer
Today, through my Academy and advisory work, I spend time helping entrepreneurs, executives, and thought leaders understand how to communicate their experiences in ways that are meaningful to others.
And one of the biggest challenges I see is that people are often far more comfortable talking about what they do than why they do it.
Ask an entrepreneur to describe their company, and they’ll usually have an answer ready. They can explain their services, their target audience, their growth strategy, and what makes their business different from the competition.
Ask them what success means to them personally, and the conversation can become much more interesting.
Not because they don’t know the answer, but because they may not have stopped to consider it in a long time.
I think this is particularly true for high achievers. We become so focused on reaching the next milestone that we rarely revisit the reasons we started in the first place.
The business grows. The responsibilities increase. The opportunities become bigger. And before we know it, we’re measuring our lives against goals we established years ago, perhaps when we were very different people.
But what happens when those goals no longer reflect who we’ve become?
What happens when the title you’ve worked toward no longer brings the satisfaction you expected? Or when the company you’ve built is successful on paper, but the life surrounding it feels increasingly disconnected from what matters to you?
Those aren’t easy questions, especially for people who are accustomed to having the answers.
But I believe they’re worth asking.
The Story Behind Your Success Is What People Remember
There’s another reason I love this question, and it has everything to do with storytelling.
After more than three decades behind the editor’s desk, I can tell you that accomplishments alone rarely make someone memorable.
I’ve read thousands of professional biographies filled with impressive titles, awards, revenue figures, and industry recognition. Those details establish credibility, and they certainly have their place.
But they don’t necessarily create a connection.
What makes someone interesting is often the perspective they’ve developed through those experiences.
Consider the difference between an entrepreneur telling you they’ve built a multimillion-dollar company and that same entrepreneur explaining how building it changed their understanding of success.
The first tells you what happened.
The second begins to tell you who they are.
And for a journalist, that’s where the more compelling story often begins.
When I interviewed people like Daymond John and Tony Robbins, I wasn’t simply looking for another impressive quote about achievement. I was interested in the thinking behind their success, the values that shaped their decisions, and the lessons readers could apply to their own lives.
That’s what gives a story depth.
And it’s something I encourage every leader to consider when developing their own personal narrative.
You don’t need to be famous or wealthy to have a story worth telling. You need to understand what your experiences have taught you and why those lessons might matter to someone else.
I’ve Had to Reconsider My Own Definition, Too
There’s a personal reason this question continues to resonate with me.
For much of my career, success was closely connected to professional achievement. I loved journalism, I loved publishing, and I took tremendous pride in the magazines I helped build and lead. Becoming an Editor-in-Chief and later serving as Chief Content Officer of SUCCESS Enterprises represented significant milestones in a career I’d spent decades developing.
Those accomplishments still mean a great deal to me.
But life has a way of changing your perspective.
Surviving a heart attack at 39 forced me to think differently about my health, my priorities, and the pace at which I was living. Becoming a mother shaped my understanding of responsibility and what I wanted my children to learn from watching me. And more recently, stepping away from a C-suite role to build my own businesses has challenged me to reconsider the relationship between professional identity and personal fulfillment.
For years, I was the person behind the title. The editor making decisions, leading teams, and helping shape the stories of other successful people.
Now, in many ways, I’m writing a new chapter of my own.
And I’ve realized that success, for me, has become less about the position I hold and more about the freedom to do meaningful work, the people I get to share my life with, and the impact I can make through the experiences I’ve accumulated.
I still have ambitious goals. I still love building things, creating opportunities, and working with extraordinary people. That part of me hasn’t changed.
What has changed is my understanding that achievement and fulfillment aren’t necessarily the same thing.
And I don’t believe we should have to choose between them.
Maybe It’s Time to Ask Yourself the Same Question
When I think back on all those conversations at SUCCESS, what strikes me most is how differently people defined a word we use so casually.
Success.
We talk about it constantly in business. We measure it through revenue, promotions, growth, influence, and recognition. We celebrate it publicly and compare ourselves to other people’s versions of it, often without realizing we’re doing so.
Yet the people who have achieved extraordinary wealth and recognition frequently speak about success in much broader terms.
Impact. Mindset. Freedom. Relationships. Purpose.
Things that don’t always fit neatly into a financial statement or professional biography.
That’s what I find so interesting.
And it’s why I believe every entrepreneur and leader should take the time to develop their own answer, rather than simply adopting the definition their industry, organization, or social circle has created for them.
If I were sitting across from you today, preparing to write your story, I’d probably ask you the same question I asked so many of the people I interviewed throughout my career.
What is your definition of success?
Not the answer you think sounds impressive. Not the one you believe your employees, clients, or peers want to hear. And certainly not the version that looks best on LinkedIn.
Your answer.
Because somewhere in that response, I suspect there’s a story far more interesting than your job title, your latest achievement, or the size of your business.
There’s a story about what you value, what you’ve learned, and who you’ve become along the way.
And after all these years as a journalist, I still believe those are the stories worth telling.
Your Story Is More Than Your Accomplishments
In my digital guide, Sculpting Your Story, I share the editorial insights I’ve developed over more than 30 years of interviewing leaders and shaping stories for major publications. It’s designed to help entrepreneurs, executives, and thought leaders look beyond their professional biographies and uncover the experiences, perspectives, and defining moments that make their stories worth sharing.
Learn more at KerrieLeeBrown.com.