If you’ve ever felt that quiet tug for “something more,” this episode is for you.
I’m sharing the story behind my movement — the real one. The childhood threads, the detours, the pivots, the heartbreaks, and the unexpected joys that shaped the work I do today with women who are ready to serve with heart instead of hustle.
From growing up on an Iowa farm with older parents and a big imagination… to climbing the corporate ladder, navigating burnout, finding my footing in direct sales, and rebuilding again after a sudden company closure — every chapter pointed me toward one thing: helping women lead with joy, purpose, and authentic connection.
Inside this episode, I talk about:
- The early influences that shaped my love for humor and connection
- The corporate moment that sparked my first major pivot
- How Traveling Vineyard became a catalyst for community and confidence
- Why hustle culture stopped aligning with my values
- The unexpected gift inside a sudden career ending
- The birth of the Sipper Club, Wine Camp, and Serving Superstars
- Why this work has become a movement, not just a business
Key Topics We Explore:
- Joyful, service-centered leadership
- Mindset shifts that create clarity and confidence
- Community, connection, and the power of women supporting women
- Rebuilding identity after big life or career transitions
- Growing a business at the pace of peace
If this episode resonates and you’re ready to explore what’s next for you, I’d love to connect. Schedule a free Discovery Call: pennyforyourshots.com/call
Want support growing your business? Book a free Discovery Call with Penny: https://tidycal.com/pennyforyourshots/discovery-call
Wine Camp 2026: Join the list or save your spot:
https://www.pennyforyourshots.com/winecamp
Become an Insider for weekly updates, tips, inspiration, and episode extras:
https://www.pennyforyourshots.com/insider
Love cocktails + community? Join the Sipper Club:
https://www.pennyforyourshots.com/sip
Explore all things Penny: coaching, podcast, events, & more:
https://www.pennyforyourshots.com
Follow Penny on Instagram: @penny4yourshots
Or on Facebook: Penny (Kuhlers) Fitzgerald
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