Leadership That Inspires: A Conversation with Stephen Levy

Hosting the Success Builders Podcast has allowed me to sit down with some truly remarkable individuals, and my recent guest, Stephen Levy, was no exception. Stephen’s story is one of transformation, authenticity, and purpose-driven leadership, and it’s a conversation I’m excited to share.

Stephen’s insights into leadership are both refreshing and deeply impactful. During our conversation, we explored what it takes to lead purposefully, embrace self-discovery, and foster respect within teams. 

Stephen's journey offers invaluable lessons if you want to grow as a leader and make a meaningful difference in your organization.

Tune in to our full conversation:

A Turning Point That Redefined Purpose

Stephen Levy’s career journey is anything but conventional. Before founding Dare2Be Coaching and Beyond, Stephen spent years working in the fashion industry—a field he candidly admitted was far removed from his interests. 

What kept him going wasn’t the business itself but the people. Stephen had a knack for nurturing growth and unlocking potential in his team members, even when the work didn’t ignite his passion.

At the age of 54, everything changed. Stephen described a pivotal moment on a routine drive home—one of those quiet moments of reflection that hits you unexpectedly. He realized he wasn’t fulfilled. That moment of clarity sparked six months of coaching and introspection. Stephen uncovered a life-changing truth: his true calling was to help others discover their uniqueness and embrace their potential.

This realization led to Dare2Be Coaching and Beyond, a platform that guides leaders through self-discovery and growth. Stephen’s story is a powerful reminder that it’s never too late to realign your life with your passion.

The Core of Effective Leadership

During our conversation, Stephen shared what he believes are the three pillars of effective leadership. These principles weren’t just theoretical ideas; they were hard-earned truths that Stephen had seen in action time and time again.

1. Self-Awareness: Great leadership starts with understanding yourself—your strengths, limitations, and how you show up for others. Without self-awareness, it’s impossible to lead effectively.

2. Respect for Differences: Stephen emphasized the importance of recognizing and valuing each team member's unique skills and perspectives. True innovation and collaboration happen when leaders create an environment where differences are celebrated, not just tolerated.

3. Empowering Growth: At the heart of Stephen’s approach is a commitment to helping others grow. A leader’s success is intrinsically tied to their team's success, and empowering others is the ultimate measure of impactful leadership.

   
   

What stood out most was how Stephen connects these principles to his coaching philosophy, which focuses on guiding leaders to create environments where their teams can thrive.

Overcoming Barriers and Embracing Courage

One of the most inspiring parts of our discussion was Stephen’s openness about the challenges he faced in his journey. Starting a business at 54 came with its share of doubts and fears. Many of us can relate to those internal narratives that tell us we’re too old, too inexperienced, or too “something” to make a change.

Stephen’s story is a testament to the power of courage and perseverance. Instead of letting those doubts hold him back, he leaned into his strengths and allowed his experiences to guide him. His advice to anyone feeling stuck? Begin with your current strengths and have faith in the process, as growth is achievable at any stage of life.

Stephen’s Tailored Approach to Coaching

What makes Stephen’s coaching style unique is his ability to balance structure with flexibility. While he follows a proven framework to guide his clients, he also tailors his approach to meet each leader’s needs.

Stephen’s framework focuses on four key areas:

• Leading Self: Understanding and leveraging your natural strengths.

• Leading Change: Adapting to challenges and driving transformation.

• Elevating Team Excellence: Building cohesive, high-performing teams.

• Igniting Growth: Achieving long-term success through intentional actions.

Stephen often incorporates tools to support self-discovery, which helps leaders uncover their natural talents and behavioral patterns. But what I found particularly impressive was Stephen’s adaptability. He recognizes that every leader’s journey is different. Some thrive with detailed action plans, while others benefit from a more flexible, exploratory approach.

Respect as the Foundation of Great Teams

One of Stephen's most powerful insights was about the role of respect in leadership. Respect isn’t just about being polite; it’s about creating a culture where everyone feels valued and heard.

When leaders model respect, it has a ripple effect throughout the organization. Teams that feel respected are more likely to trust each other, collaborate effectively, and bring their best ideas. Stephen has seen firsthand how fostering respect within a team can transform their performance, morale, and sense of purpose.

This approach to leadership isn’t always easy, but as Stephen pointed out, it’s incredibly rewarding. When leaders prioritize respect and authenticity, they create an environment where everyone—not just the business—can thrive.

Leadership as a Lifelong Journey

What I appreciated most about my conversation with Stephen was his perspective on leadership as a journey rather than a destination. There’s no point where you “arrive” and suddenly have all the answers. The best leaders are constantly learning, reflecting, and evolving.

Stephen’s journey—from a career in fashion to founding Dare2Be Coaching and Beyond—is proof that leadership is about embracing change and stepping into your authentic self. It’s about being willing to grow and helping others do the same.

A Call to Action for Leaders

If there’s one thing I took away from my time with Stephen, leadership is a deeply personal and rewarding path. It’s about more than achieving results; it’s about building relationships, fostering growth, and positively impacting those around you.

Whether you’re just beginning your leadership journey or looking to take your skills to the next level, Stephen’s insights offer a roadmap for growth. Start with self-awareness, embrace respect and authenticity, and don’t be afraid to seek support.

Leadership is a collaborative effort; the best results come when we lean on each other for guidance and inspiration.

Leadership That Leaves a Legacy

My conversation with Stephen Levy on the Success Builders Podcast was inspiring. His journey highlights the significant impact of authenticity, respect, and intentional growth on teams and organizations.

Stephen’s story highlights that leadership involves personal evolution, not just guiding others. His principles—self-awareness, respect for differences, and commitment to empowering growth—serve as a blueprint for building a lasting legacy.

Tune in to the Success Builders Podcast

Ready to uncover what it truly means to lead with purpose? Don’t miss this inspiring episode with Stephen Levy, where we dive deep into the art of authentic leadership, self-discovery, and building teams that thrive. Whether you’re a seasoned leader or just starting your journey, this conversation is packed with actionable insights to help you grow and make a lasting impact.