Why I Built This Movement for Women Who Serve With Heart

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

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Transcript

Penny Fitzgerald: ​ [00:00:00] Hello, friends. Today's episode is going to be a little different. Instead of chatting with one of my amazing guests, I'm sharing something that feels both personal and powerful. the story of how I got here. My coach recently challenged me to think about my movement, the deeper why behind what I do and who I serve.

And when I started tracing it back, I realized how many pivotal moments shaped not just my business, but the way I see [00:01:00] women service and joy. This isn't a highlight reel or a me story, it's a reminder that the things that we go through, the detours, even the heartbreaks, they all have purpose. They shape who we become and how we show up for others.

So grab your favorite drink and settle in. Let's take a walk through the moments that led me here to this movement, and of women serving with joy. Courage and heart. 

Growing up, I wasn't particularly confident, but I loved pretending to be. I found joy in make believe and in performing, especially when it made others smile or laugh. Humor became my bridge to connection, even when I felt unsure of myself. It's what helped me feel seen and helped others feel good too.

I grew up the youngest by a long shot. My brothers were already in their twenties by the time I came along. Both left for the Air Force when I was just two. One to California and the other to Okinawa. So while technically it was the baby sister it was really [00:02:00] just dad, mom and me at home on the farm in Iowa, mom and dad were much older and pretty busy doing their own thing.

Both were entrepreneurs. Dad, a grain holler, and mom had a little jewelry shop on the farm where she crafted pins and rings or repaired other people's jewelry and attended craft fairs on weekends. She was also the one who kept the house going while dad tended to the outbuildings and to the animals.

So I learned pretty early on how to entertain myself. I played with those animals, made up elaborate stories,sometimes recording them on a cassette tape player. There's a precursor to today, huh? And I spent a lot of time watching tv probably too much, especially watching shows with strong, funny women.

Carol Burnett was my queen. I adored Mary Tyler Moore and Maude too. They were smart, confident, and hilarious, and I remember thinking, I wanna be like them when I grow up. Looking back, I think that's where my love of humor and connection really began. [00:03:00] I saw how laughter could change the energy in a room, even if that room was just our living room and a black and white tv.

Those strong female entertainers didn't just make me laugh. They showed me what it looked like to be confident, expressive, and unapologetically yourself. That energy carried with me into high school where it felt natural to make people laugh or to lift them up through performance.

it was so much fun being the comic female lead in productions or leading the marching band as drum major. Anyone still have their band feet? I do. So while some people learn to hold their own living in a full, boisterous household, I learned to hold my own through humor, through storytelling, through listening and creating connection outta quiet, through performing and leading.

That's been a thread throughout my life, making people feel seen and building bridges through laughter, warmth and empathy. But like so many women, I did what I thought I was supposed to do. I went to school. I worked hard. I [00:04:00] believed that if I checked all the boxes, education, marriage, a stable job, I'd find fulfillment.

Spoiler alert, it didn't quite work out that way. College was both exciting and humbling. A wake up call in a completely different way. High school had felt comfortable and so fun for me, so I assumed college would too. What caught me off guard was not only the depth of the work, but the breadth of it, the global perspectives, the conversations that reached far beyond the farm fields of Iowa.

Growing up in a small, traditional, mostly white Christian community, my world had been familiar and comfortable. College opened my eyes to history that wasn't just facts and dates to cultures and struggles I had never even considered. It challenged me to think bigger. To question assumptions and to recognize that the world was so much broader than the one that I'd known after college came the grownup world, and with it, the pressure to be practical, my [00:05:00] first real job was in training and management in a retail setting where I quickly realized that men and women were not treated equally.

My male classmates were encouraged into leadership roles while women were steered toward administrative support. I learned fairly quickly and took pride in contributing as part of a great team. I was organized, dependable, and I made other people look good, but I wasn't building something that was mine.

I felt small and pretty insignificant. I guess that's pretty normal in a big company, and for years I put one foot in front of the other, pouring my energy into helping others succeed. Bosses, colleagues, the companies I represented as a client liaison in a support role. I was part of a dependable solutions oriented team that kept things moving and connected all of the moving parts and departments, and yet there was always this quiet voice in the background saying you were meant for more.

I didn't know what that meant and didn't always listen to it. In fact, I pushed it down [00:06:00] for a very long time. Then one day sitting in a yearly sales goals meeting with our VP of sales. Everything changed. She was handing out our goals for the next year, and none of them were realistic, but they were being forced down to her from our leadership team.

I felt my heart start to race and I quietly took my pulse. It was over 130 beats per minute just sitting there in a meeting. My body was telling me the truth before my brain would admit it. I needed to make a change. Fast. That whisper became a shout. I picked up the book, what Color is Your Parachute?

Anyone remember that? And started journaling and exploring what might come next. I began looking for something that sounded fun. The wine industry, and that's when Traveling Vineyard popped up. Thanks to a nudge from my dear friend Jennifer, who's still one of my closest friends and travel buddies to this day, 

and one of my wine campers and Sipper Club members. Now, I also began to realize how much I [00:07:00] had learned from the people around me. The mentors, the coworkers and friends who modeled leadership, collaboration, and resilience. Those shared experiences taught me just as much as the work itself, and I started to see that every role I'd held was preparing me for something bigger.

That everything I'd learned, all those years of organizing, observing, and lifting others up, it was preparing me for something bigger. I just didn't know what it was yet.

When I found Traveling Vineyard, it was like the universe was saying, here you go. This is what you've been looking for. It was the perfect combination of connection, leadership, fun, and well wine. I loved that it wasn't about sitting behind a desk or pushing papers. It was about people creating moments of joy around a shared table.

It gave me permission to show up as me again, to be creative, to laugh, to build community. What started as a side gig quickly became something more meaningful, not [00:08:00] just financially, but personally. I discovered the part of myself that thrived on helping others feel confident and capable, the part that believed in the power of women supporting women.

As my business grew, I climbed the ranks. I led a top performing team and built friendships that felt more like family. I watched women discover their confidence. Their voices and their strength, and that's when it clicked for me. This wasn't just about wine tastings, it was about transformation. I could see women light up when they realized they were good at this, that they could lead, they could teach, they could inspire.

I loved every bit of it until one day I didn't. Because somewhere along the way, the culture started to shift for a while, that masculine hustle and grind way of doing things that actually worked the mindset of just work harder, talk to more people, figure it out. You'll get your piece of the pie. but [00:09:00] over time it began to feel off.

Leadership often said that a rising tide lifts all boats, and they talked about wanting to lift and support everyone equally. It sounded great in theory, but what actually played out rewarded those who grabbed their piece of the pie and left behind those who were genuinely trying to serve the whole community.

There was talk of an even playing field, yet actions often reflected favoritism and inconsistency. And here's the thing, women have a pretty good BS meter, and this kind of culture just doesn't fly. That hustle and grind mindset leads to burnout and never works long term. It feels icky because it centers on the salesperson instead of the people you serve.

It doesn't come from a place of abundance, and it certainly doesn't move you toward your soul's purpose. That bro, marketing and peace of the pie attitude might drive short-term results, but it doesn't sustain connection. It doesn't sustain [00:10:00] joy or heart. 

The joy began to fade, replaced with corporate pressure and metrics that felt misaligned with what had made the experience so special in the first place. When the fund disappears and the focus turns to control instead of connection, you start to lose the heart of why you began.

And once I realized that I couldn't unsee it, I knew I had to pivot again, not away from serving women, but toward a way of doing it that aligned with my values and heart. What's interesting is that I didn't start my podcast with the intention of leaving traveling Vineyard. If anything, I thought the podcast would help rebuild my business there.

I believed that sharing women's stories and conversations about courage and connection might spark new energy in my team and attract more like-minded people. And honestly, it probably would have, but it would've taken longer to become what it is today. For that. I'm actually grateful that traveling vineyard ended.

When it did, [00:11:00] it gave me the space and clarity to step into something new, something that was already waiting for me. When leadership at Traveling Vineyard made the sudden decision to close the business, my career there ended in an instant. I didn't choose to step away. The choice was made for me, but instead of letting that be the end.

I saw it as my cue to pivot. I took action and that action brought clarity. What had started as a podcast meant to rebuild my business became something entirely different. It became a platform, a place where women could share their stories, be seen, and be reminded that their voices mattered. It also became the mirror I didn't know I needed.

Every conversation I had, every guest I interviewed reflected my piece of my own journey back to purpose. These women were chasing dreams, facing fears, and rediscovering who they were beyond titles, expectations, and shoulds. [00:12:00] I realized I wasn't alone in feeling that tug for more. As those conversations unfolded, I began to see a pattern.

Women were craving authenticity, not another formula for success. They wanted connection over competition, purpose over pressure, and impact over income. Around that same time, I also realized how much joy I found in creating fun shared experiences. Girlfriend Time that revolved around wine cocktails and connection.

That's how my Sipper Club was born. My first offer built around those same principles of community and joy. And another favorite from my traveling vineyard days. Our yearly convention we called Wine Camp That inspired something new too. Robin and I dreamed up our own version of that connection and creativity.

An immersive retreat for women to laugh, sip, and recharge together in wine country. Robin has since moved on to our own fitness and wellness [00:13:00] retreats, but I'm carrying that vision forward, expanding wine camp into something even more intentional and joy filled. and that's when the idea for serving superstars began to take shape.

 I wanted to create a space where women could build businesses that felt good. Not forced a space that celebrated their gifts, honored their values, and gave them tools to serve without losing themselves in the process. The work wasn't about teaching tactics.

It was about transforming mindsets, about reminding women that service is powerful and that it's okay to grow at the pace of peace. Leaving traveling Vineyard wasn't an ending. It was an evolution. It was the moment I stopped chasing other people's definitions of success and started helping women design their own.

I also realized that when we infuse fun and joy into what we do, everything flows more easily. The energy we create attracts more of what we love. [00:14:00] Serving people brings joy. And that joy fuels momentum. It's not just a business strategy, it's a mindset and a culture that keeps us aligned with our purpose.

For me that joy often looks like girlfriend, time, laughter, and connection. the kind that fills your cup and reminds you why you do what you do. And that's when my mission became clear. I'm here to lift women up. Help them find their voices and show them when they lead from service and joy abundance follows.

Somewhere along this journey I realized that what I was building wasn't just a business. It was a movement. A movement grounded in service, joy, and authentic connection because women are hungry for spaces where they can show up as their whole selves, where they don't have to hustle harder or shout louder to be seen through the podcast, the Sipper Club, wine camp, and serving superstars.

I've watched what happens [00:15:00] when women gather and lift each other up.they rediscover their confidence, their creativity, and their spark. They begin to dream again, not in a lofty, abstract way, but in a grounded, actionable way. They start to take those small steps that lead to big shifts, and when one woman does that, it gives permission for others to do the same.

That's the heartbeat of everything I do now. Building community, creating joyful experiences and helping women serve from a place of abundance rather than scarcity. Because when we lead with joy and generosity, we change everything, not just for ourselves, but for everyone we touch. I believe this is how we rewrite what success looks like for women in business by focusing less on competition and more on collaboration, less on achievement, and more on alignment.

Less on being everything for everyone and more on being true to [00:16:00] ourselves. SoAs I look ahead to the next round of serving superstars launching in February of 2026, that's the invitationto every woman who's ready to stop selling and start serving, to find joy again in her work, to use her gifts with confidence and to know that she's part of something bigger.

A movement of women choosing service over sales, purpose, over pressure and joy over judgment. That's what we're doing here, and I couldn't be more grateful to be doing it together. If today's conversation resonated with you and you're ready to explore what's next, whether that's finding more joy in your business, clarifying your purpose, or discovering how we can work together, I'd love to connect with you.

Schedule a free Discovery Call at pennyforyourshots.com/call. And if you're not already hanging out with me on Instagram, come join the fun @penny4yourshots. That's at @penny4yourshots. it's where [00:17:00] I share stories, inspiration, and a few behind the scenes sips of what's coming next.

And before we wrap up today, I wanna raise a virtual glass to you. Or a real one. Cheers to your courage for listening to that nudge, for showing up for yourself and for serving in ways that make a difference. Cheers to the joy we create, the community we build, and the ripple effect that follows when women choose to lift one another up.

Cheers to your success and cheers to us. 

To book a call: pennyforyourshots.com/call