In life and leadership, there are Moments that Matter—the ones that define our paths, shift our perspectives, and push us to grow. These moments don’t wait for us to be ready; they arrive unannounced, demanding action.
As a leader in some of the world’s most demanding industries, I’ve seen firsthand how courage and intentional choices inspire teams to exceed expectations. From the streets of Oakland to the sidelines of the NFL to the boardrooms of Fortune 500 companies, I’ve learned one powerful truth: empowered people empower others. When leaders embrace their own courage and authenticity, they create environments where teams can thrive and organizations can achieve extraordinary results.
Through my journey, I share actionable strategies that help executives inspire self-leadership in their teams, unlocking potential at every level. Imagine what your organization could achieve if every leader, from the front lines to the C-suite, embraced the courage to lead with purpose. That’s the power of choice over chance—and the message I bring to every stage.
I help women leaders recognize the three Moments that Matter to thrive in business and life. Miss them, and you stall. Crush them, and you SOAR!
It’s all you need to break free from what or who is holding you back and break through into what you really want. Seven Seconds of Courage is the key to unlocking moments that matter. The first six seconds are filled with fear, hesitation, and doubt. But in that seventh second—when emotion gives way to clarity—you choose courage. Decisions are made, relationships are forged, and futures are defined. Take 30 seconds now and watch, it's choice not chance that can change your life!
It is choice, not chance, that changes your leadership. It is choice, not chance, that changes your legacy, and it is choice, not chance, that changes your life. Still, we often leave our leadership, careers, and even our lives to chance. Stop chasing, and start choosing to be the best leader you can be. Stop chasing success and start choosing significance. Stop chasing external validation and start choosing to see your value within; it’s the only way to lead and live with intention.
“Coming from Charlene, who has the professional and personal experience to back it up, this talk was motivating and empowering.”
Every story has a beginning, and mine starts with a spark of courage—a single choice that changed everything. My journey from the ballfield to the boardroom is a testament to the power of resilience, empowerment, and intentional action.
In this video, I share pivotal moments that shaped my life, from the sidelines of the NFL to the highest levels of corporate leadership to triumphing over two cancer diagnoses within six months of each other. It’s not just my story—it’s a call to action for anyone ready to embrace their power, lead with purpose, and inspire others to do the same. My future isn’t written yet. Let’s explore how you can take control and write your next chapter.
Charlene Wheeless isn’t just a leader—she’s a storyteller, trailblazer, and voice of empowerment. From the sidelines of the NFL to the boardrooms of Fortune 500 companies, she’s spent over three decades breaking barriers and building bridges in industries where few women, let alone Black women, had ever led.
As the founder and CEO of Charlene Wheeless LLC, Charlene shares her hard-won wisdom through keynote speeches, leadership coaching, and her bestselling book, You Are Enough!. She helps organizations create cultures where people—and businesses—flourish by embracing bold choices, authenticity, and impact-driven leadership.
Charlene’s journey proves that success isn’t just about where you’ve been—it’s about where you choose to go next.
Charlene is pictured with Lt. General Clark, superintendent of the U.S. Air Force Academy, and several female cadets and security force members.
Charlene has spoken to/performed for audiences exceeded 100,000 people over her speaking and her performance career.
100,000 People
Through her work, Charlene has empowered over 1,000 professionals and women leaders, helping them unlock their potential and drive success in their careers through her leadership development journey programs
1,000+ Leaders
Charlene has delivered impactful speeches at over 100 events, sharing her insights and strategies with diverse audiences across the globe.
100 Events
Charlene has coached more than 8,000 hours with leaders, executives, and early career professionals, and helped more than 50 organizations.
8,000+ Hrs
“She’s not a whiner and has no regrets, she offers a view of corporate America that will open your eyes.”
Building Better Teams One Choice at a Time
Cohesive leadership teams drive results, but building that cohesion isn’t a quick fix—it’s a journey. 🚀 In my new article, I talk about how intentional choices, ongoing learning, and a little bravery can transform any team. And speaking of bravery, I’m spotlighting a friend’s new book too! 📖 Dive in!
The Power of Shared Narratives
“You can’t truly see the world clearly until you see it through everyone’s eyes.” When this sentiment brushed across my ears recently, it lingered, gently nudging at a wisdom that feels both timeless and urgently contemporary. Our vision, often, is singular – shaped by our experiences, our prejudices, and our blind spots. 
Is Feedback Really a Gift?
In the professional world, feedback is often heralded as a quintessential personal and organizational growth tool. "Feedback is a gift," they say. But let's be honest, how many of us have unwrapped this so-called "gift" to find something less than pleasant inside?
Leadership by Choice: Choose Your Destiny
You've likely heard the phrase, “Every champion has a coach.” Look at any elite athlete - Serena Williams, LeBron James, or Lionel Messi - and you'll quickly realize they didn't achieve greatness solely on their own. So, if athletes at the pinnacle of their sport seek coaching, why should leaders be any different?
Rethinking the American Dream and The Decline of Hustle Culture
Once upon a time, in a land fueled by caffeine and ambition, the American Dream looked a lot like steady jobs, suburban houses, the pursuit of material prosperity, and maybe even a golden retriever named Buddy. Today? Not so much. 
Overcoming “Traditional” Structures
Navigating traditional environments as an individual that is considered anything but “traditional” is the everyday reality for many. Finding personal value during this process is an added complication. 
Keynote & Inspirational LEADERSHIP Speaking
Many organizations struggle to cultivate effective leaders who can inspire and drive their teams toward success. Low employee engagement and a lack of a positive organizational culture are making even the most stalwart companies subject to disruption.
My keynotes and approaches emphasize a culture of choice, not chance, solving issues of employee engagement and decision-making efficiency. Together, we create an environment where employees are motivated, involved, and autonomous, leading to better performance and lower turnover.
Build Resilience and overcome challenges with Leadership Programs and Executive Coaching
Organizations and individuals often struggle with building resilience and navigating through personal and professional challenges.
My personal journey of transformation and reinvention provides a powerful blueprint for overcoming adversity and thriving in the face of challenges. In addition to my coaching credentials, I leverage my expertise and experiences, to provide valuable insight and practical solutions to organizations and individuals looking to develop their unique path to success.
