Creating Space for Women Entrepreneurs to Rewrite Their Money Stories
What You Need to Know
Women entrepreneurs need more than “girl boss” advice. Creative business owners have been told to hustle harder and figure it out alone, while too many honest conversations about pricing, profit, taxes, and wealth-building happen behind closed doors.
Financial confidence isn’t built from information alone. Our money stories shape how we price our services, advocate for our work, and create sustainable businesses.
Beautiful, intentional spaces can hold big money conversations. Experiential financial wellness blends education, reflection, and community to help entrepreneurs explore their relationship with money.
Retreat Summary
Partner: Jeannene Jones-Rupert of Intentionally Tabled and The Creative Collective
Creative Vendors:
Photography: Paloma Havlik Photo
Floral Design: Mosaica
Stationery Design: Shaytonery Designs
Linen & Charger Rentals: Detroit Verde
Location:The War Memorial, Grosse Pointe, Michigan
Role: Keynote Speaker & Workshop Facilitator
Topics: Money stories, emotional relationship with money, entrepreneurship, financial confidence, pricing, financial boundaries, women and wealth
Audience: Creative women* entrepreneurs in the wedding and events industry, including photographers, florists, planners, coordinators, hair and makeup artists, and designers who are interested in building confidence with money and wealth.
*The use of “women” is inclusive because gender is nuanced and expansive: this event welcomed cis women, trans women, and gender-expansive people who connect with women-centered spaces and conversations.
A Beautiful Space for a Money Conversation
The room was stunning. Playful, textured flowers designed by Mosaica poured from the tables onto the floor. Event-specific, custom stationery from Shaytionery welcomed each guest. Every detail felt intentional, warm, and inviting. Which was perfect. Because we were about to talk about something most people would rather avoid.
Money.
As creative entrepreneurs, the women in this room spend their careers creating meaningful, memorable experiences for other people. They design wedding days, capture once-in-a-lifetime moments, and ensure that their craft is executed perfectly so their clients can be present.
This event was created to provide them with a warm, inviting, and intentional space. The Women’s Wealth Retreat was hosted by Jeannene Jones Rupert of Intentionally Tabled and The Creative Collective. This wasn’t a stuffy business workshop where people sat through slides about profit margins while sipping burnt coffee. The day blended practical financial education with community, reflection, and connection, creating space for both the emotional and practical sides of money.
My Role as Keynote Speaker
I opened the retreat by normalizing something that so many of us experience: feeling uncomfortable when we talk about money. We often interpret discomfort as a sign that something is wrong. But many times, discomfort is a sign that we’re doing something new, meaningful, or different. And learning to tolerate a little discomfort can help us do the important money work.
As a financial therapist, my role was to help attendees explore their emotional relationship with money and how those beliefs showed up in their businesses. Entrepreneurial money stories can help us, but sometimes they can hold us back or keep us stuck.
Through journaling, reflection, and small group conversations, attendees explored questions like:
How is my current money story supporting my business?
How is my current money story limiting my business?
What beliefs about money, success, or wealth am I ready to rethink?
For many creative entrepreneurs, these stories centered on anxiety or fear about charging for their work. “I can’t charge that much because…”People finished that statement differently, ranging from “I don’t want to leave people behind” to “my peers will think I’m greedy,” but the theme was shared. So many creative entrepreneurs are incredibly talented at seeing the value in their clients and peers, but have a harder time recognizing and charging for the value of their own work.
Building Sustainable Creative Businesses with the Social Enterprise Model
Creative entrepreneurs are often exceptional at caring for others: anticipating needs, noticing the teeny details, and answering clients' questions no matter the time of day. But that care can turn into burnout without the appropriate guardrails. When a money story isn’t serving us, customer service can turn into overworking, undercharging, avoiding financial tasks, or constantly putting business needs ahead of personal wellbeing.
During my session, we explored the sweet spot where your strengths, values, and financial sustainability intersect, the heart of the Social Enterprise Model. It’s in this space that purpose-driven businesses can see how financial stability isn’t a barrier to creativity, but a foundation for it to thrive.
Emotional + Practical Financial Wellness
One of my favorite parts of this retreat was how intentionally the day was structured, connecting emotions and numbers.
I opened the day by helping attendees understand the stories, beliefs, and emotions shaping their financial decisions. From there, money coach Jillian Todd helped entrepreneurs explore how to manage business finances with unpredictable income and create more stability amid the natural highs and lows of entrepreneurship. Then, Emily Ersher of The Creative CPA shared tax-planning strategies to help small-business owners feel more prepared and less stressed about quarterly and annual taxes.
In both of these practical sessions, the speakers made sure to address how emotions show up in decisions that affect cash flow and taxes.
Releasing Old Money Stories and Planting New Ones
After a full day of learning, reflecting, and connecting, I invited attendees to identify the money beliefs, habits, or stories they were ready to release. Then attendees created a new money story they wanted to cultivate, something they could physically tuck away and rediscover later.
Some attendees chose to share what they were releasing and planting with the group; others wanted to keep them private. But the takeaway was that they all were taking a practical and emotional approach to improving their relationship with money, so they could do more good in the world through their creative businesses.
Attendee Reflections & Impact
The day’s impact went beyond financial strategies. Attendees reflected on the importance of having a supportive space to talk openly about money, business, and wealth-building.
As Candace Wojcik, a luxury hair and makeup artist who founded Pop + Coh, shared:
“The retreat was created to dismantle the stigma around money. The incredible speakers shared valuable knowledge to help us women-owned businesses to prepare for retirement, become more comfortable with taxes, and learn ways to invest for our futures in our personal lives and business. This power-packed event was a once-in-a-lifetime experience, and I feel so incredibly grateful for the opportunity!”
Luxury bridal makeup artist Asil Dawod reflected on the connection created throughout the retreat:
“I walked into this retreat hoping to learn, grow, and gain clarity around my business and finances, and I left feeling inspired by the incredible women in the room. Every conversation, every story, and every speaker reminded me that growth starts with being willing to learn. So grateful I had the opportunity to be part of such a beautiful day. Lindsay’s energy was so caring.”
For Megan Hannon, a Michigan and destination photographer, the power was being in community with other women entrepreneurs having these conversations together, “I had the most incredible day learning about money. Being in rooms with women that uplift and empower other women is truly remarkable.”
Partner Perspective
For Jeannene Jones-Rupert, Founder + Creative Director of Intentionally Tabled and The Creative Collective, bringing a financial therapist into the retreat experience was intentional.
“Lindsay's holistic approach to financial advice was one of the biggest reasons I wanted to bring her into the event. Given that we were hosting a financial retreat for women creative business owners, I wanted Lindsay's approach towards rewriting our money story since so many women struggle with barriers towards pursuing financial wealth.”
One of the biggest takeaways for Jeannene was helping attendees rethink the idea that their values and financial success have to compete with one another.
“The biggest takeaway was Lindsay sharing about the Social Enterprise Model and really helping the attendees understand that they can incorporate their values into creating wealth for themselves.”
Beautiful Spaces Can Hold Big Money Conversations
A huge thank you to Jeannene Jones Rupert of Intentionally Tabled and The Creative Collective and every partner who helped create such an intentional experience. It was a gift to be a part of such a supportive space to talk about wealth. For other organizations considering bringing a financial wellness experience into their event, retreat, or community, Jeannene shared:
“If you want a dynamic speaker who can genuinely get people comfortable talking about one of the most uncomfortable topics, then Lindsay is an amazing asset to your event!”
If you’re planning an intimate retreat, non-stuffy leadership getaway, or customized brand activation, please reach out! I partner with organizations, founders, and communities to create actionable, memorable emotional financial wellness experiences.