#038: From Imposter Syndrome to Inner Confidence - The Secret to Great Retail Leadership with Sherry Winn

Leadership isn’t just about guiding others, it’s about first leading yourself with compassion, courage, and honesty. 

In this inspiring conversation, Cathy Donovan Wagner sits down with Sherry Winn: two-time Olympian, national championship-winning coach, bestselling author, and founder of The Winning Leadership Company. Sherry has empowered thousands of executives at global brands like Adobe and Edward Jones, and captivated audiences of thousands with her transformative message.

Together, they explore how self-awareness, resilience, and self-care shape true leadership and invite you to see your own potential and lead with heart.

What You’ll Learn in This Episode:

• Why are failures essential for growth and meant to be embraced?
• Everyone experiences imposter syndrome - It means you’re leveling up.
• Why you should view obstacles as adventures rather than setbacks
• The importance of self-care in effective leadership.

Key Takeaways:

• [03:05]: The Journey of Greatness and Failure
• [09:32]: Imposter Syndrome and Self-Awareness
• [21:03]: The Importance of Self-Care in Leadership
• [26:29] Overcoming Fear in Leadership

Resources & Links

• Sherry Winn’s Winning Leadership: 7 secrets to build and keep a loyal team of champions!
• Connect with Sherry Winn on LinkedIn and book a free 45-minute “rant & rage” and visit her website.
• You’re not building just any store, you’re creating an experience, a legacy, a life that’s richer in every way. Let’s make sure the business side supports that vision. Apply for your free Gameplan Call and we’ll talk through what’s working, what’s not, and your most profitable next move.
• Want a behind-the-scenes look at how our top clients grow profit without burning out? Our free training, Beyond Busy: 3 Shifts to Reclaim Your Time and Boost Store Income, walks you through the exact Profit Roadmap we use in Profit Club, focusing on your role as CEO, CIO, and CFO to grow a business that’s both profitable and sustainable.

Your Millie Moment:

• Reflect on one recent setback and write down what it taught you.
• Notice when imposter syndrome shows up and gently challenge it with truth.
• Choose one small act of self-care each day, even five quiet minutes.
• Reframe one obstacle you’re facing as an adventure instead of a roadblock.

Little by little, these small steps build the courage and resilience true leadership requires.

Connect with ambitious store owners in the Richer Retailer Facebook Group.

Share this episode with a fellow store owner and help them tackle cash flow challenges!

💚 Remember: True leadership starts long before anyone is watching. It begins in quiet moments of honesty, courage, and compassion toward yourself. Remember: every failure can fuel growth, every doubt can spark self-awareness, and every act of self-care makes you stronger for those you lead.