Catching Up and Connections: A Conversation with Jason Hewlett

Recently, I had the pleasure of reconnecting with my good friend Jason Hewlett, someone I’ve known for about 16 or 17 years now. Like many adult friendships, we’ve had times of connecting and losing contact, but it’s always inspiring to catch up and reflect on the journey we’ve shared. Our conversation took us through memories, professional growth, and the powerful role connection plays in our lives.

From the National Speakers Association to Shared Stages

Jason and I first met through the National Speakers Association in Salt Lake City. I vividly remember the meetings on the 18th floor of the Zions Bank building, overlooking the valley—a gathering place for incredible speakers like Mark Eaton and Chad Hymas. Jason recounted how he first met me when I was in a wheelchair, and how he was immediately drawn to my story. One of my memorable moments was when I stood during a speech for the first time—rolling back my wheelchair and stepping up, a moment Jason described as “Lazarus arise,” filled with hope and drama.

Jason’s Journey: From Entertainer to Motivational Speaker

Jason started as a comedic entertainer, doing impressions and music performances with Las Vegas-quality shows. Over time, as his voice suffered from all the singing and he did hundreds of shows annually, he transitioned into keynote speaking—still incorporating music and comedy, but with a stronger leadership and motivational focus. His evolution highlighted the balance of passion, practicality, and professionalism, which resonated with me on my own speaker journey.

The Power of Preparation and Audience Connection

We talked extensively about the importance of preparation. I shared my experience developing a day-long workshop full of engagement and practical insights, a challenge that required hundreds of hours of prep. Jason echoed the sentiment, emphasizing that great speakers know how to expand or condense material depending on the audience and setting. The connection with the audience is everything, whether you’re delivering a keynote or a business update.

Stories That Inspire and Humble

Jason shared a touching story about preparing a song for a friend's funeral—hours of preparation for a deeply meaningful, brief moment on stage that helped a family heal. It reminded me how much goes on behind the scenes for moments that can change lives. We also reminisced about people in the speaker community, including moments with iconic figures like Mark Eaton and Chad Hymas, reflecting on the impact of connection and shared purpose.

Humor, Authenticity, and the Journey Forward

Our chat was peppered with humor, including stories of my brothers joking about me in my wheelchair and the challenges of airport travel without mobility aids. We shared laughs and insightful moments about how authenticity and willingness to embrace all parts of our stories make us stronger communicators. Jason’s journey from entertainer to heartfelt motivational speaker inspired me to continue growing and connecting authentically.

Final Reflections

Reconnecting with Jason reminded me that in life and career, it’s those genuine connections—whether through shared challenges, humor, or passion—that fuel our greatest growth. Whether on stage or in everyday life, embracing our stories with vulnerability and confidence engages others in ways words alone can’t. I’m grateful for friendships like Jason’s and excited for the many connections yet to come.

Thank you for joining me in reflecting on the power of connection, resilience, and authentic storytelling.