Summary

In Episode 16 of Never Stop Dreaming BIGGIE, I'm tackling the biggest struggle facing multi-passionate women entrepreneurs—feeling scattered and overwhelmed by traditional productivity advice that just doesn't work for creative minds like ours. If you're tired of having 27 browser tabs open, waking up with 15 business ideas before 9 AM, and feeling like you're the only one who can't "just focus on one thing," this episode is your validation and solution.

I'm sharing the organization secrets that helped me manage 20,000+ person festivals while running multiple businesses, revealing why energy-based planning beats time management and how to create systems that work WITH your multi-passionate brain, not against it. Plus, I'm joined by the incredible Jen El-Haddad from Jennifer Mary Photography, who shares her inspiring journey from corporate layoffs to building a thriving branding and wedding photography business in Charleston.

Jen opens up about her "come-to-Jesus moment" at a church conference that changed everything, her approach to authentic community building through events like Stretch and Mingle, and why professional photography should be your second business investment. This is the "G" in BIGGIE—Grow—through challenges by creating systems that honor how your brain works and building community that supports your biggest dreams.

Instagram

@neverstopdreamingbiggie and @angelpholmes

Learn More

🌴 The Holmestead Bar & Retreat

👩‍💼 The Brighter Side Society

📧 Email: angel@neverstopdreamingbiggie.com

🌐 Website: sipindipity.com

Takeaways

• Understand why you're not broken—you're just a multi-passionate women entrepreneur
• Learn energy-based planning strategies that work for ambitious women
• Discover business organization systems for managing multiple projects
• Master the profit priority matrix concept for focusing on what matters most
• Explore Jen's inspiring corporate to photography entrepreneur journey
• Recognize the importance of professional branding photography for business success
• Build authentic community networks that grow your business organically
• Apply collaboration over competition principles in women's entrepreneurship
• Create accountability partnerships that keep multi-passionate women on track
• Transform scattered energy into laser-focused business action through proven systems

Chapters

00:00 Introduction - The 27 Browser Tab Reality

02:30 The "G" in BIGGIE: Growing Through Challenges

04:45 Why Multi-Passionate Women Feel Scattered

10:15 Festival Organization Secrets for Business Systems

15:30 Energy-Based Planning vs Time Management

20:25 Guest Introduction: Jennifer Mary Photography

22:10 Jen's Corporate to Photography Journey

28:15 The Power of Authentic Community Building

34:45 Professional Photography for Business Branding

40:30 Collaboration Over Competition Philosophy

45:15 The Brighter Side Society and Accountability

Summary

In Episode 15 of Never Stop Dreaming BIGGIE, the Holmes boys finally take the mic! Join me for this special live recording with my husband Brian (the famous "Director of No Fun") and son Chase as we answer real questions from The Brighter Side Society community. This unfiltered family Q&A gives you exclusive access to our Caribbean bar planning process, business strategies, and authentic entrepreneurial journey.

You'll get the inside scoop on our upcoming island-hopping trip to scout locations for The Homestead Bar & Retreat in Bequia, Barbados, or Grenada. Brian shares why we're leaving the hurricane zone, what we're looking for in the perfect sailing community, and our timeline for spending 6-9 months per year running our disaster relief bar. Plus, Chase undergoes his hilarious "job interview" for entertainment director (complete with toilet cleaning duties) while we break down The Brighter Side Society membership benefits and upcoming price changes.

Whether you're curious about international business ventures, struggling with imposter syndrome as a female entrepreneur, or wondering how family support systems fuel big dreams, this episode delivers both entertainment and practical insights. This is the "B" in BIGGIE—Believe—that your wildest dreams are meant for you, especially when you have the right people cheering you on.

Instagram

@neverstopdreamingbiggie and @angelpholmes

Learn More

🌴 The Holmestead Bar & Retreat

👩‍💼 The Brighter Side Society

📧 Email: angel@neverstopdreamingbiggie.com

🌐 Website: sipindipity.com

Takeaways

• Discover the three Caribbean islands being considered for The Homestead Bar & Retreat
• Learn complete details about The Brighter Side Society membership ($75/month)
• Master strategies for overcoming imposter syndrome through community support
• Understand how family business dynamics strengthen entrepreneurial ventures
• Explore the disaster relief mission driving The Homestead Bar concept
• Navigate international business planning and island selection criteria
• Recognize the importance of sailing communities for bar location success
• Apply manifestation techniques through faith and consistent visualization
• Build supportive partnerships that fuel rather than limit your dreams
• Create authentic family business content that connects with audiences

Chapters

00:00 Live Setup & Caribbean Bar Introduction

02:30 Meet Brian & Chase: The Holmes Boys

05:45 Island Hopping Plans: Bequia, Barbados, Grenada

08:20 Chase's Entertainment Director Job Interview

12:15 The Brighter Side Society Membership Breakdown

18:30 Homestead Bar Timeline & Investment Details

22:10 Overcoming Imposter Syndrome as Female Entrepreneurs

28:45 Family Business Dynamics & Partner Support

32:20 Community Building & Women Supporting Women

35:50 Caribbean Trip Planning & Attorney Guidance

38:15 Closing Thoughts & Community Appreciation

Summary

In Episode 14 of Never Stop Dreaming BIGGIE, I'm getting vulnerable about my entrepreneurial journey from founding the Charleston Wine & Food Festival to making the difficult decision to close Like Minded Charleston and focus on building The Brighter Side Society globally. This solo episode explores business pivot strategies, community building secrets, and how faith-based decision making led to creating multiple successful ventures from scratch.

You'll hear the real story behind building events with billion-dollar economic impacts, losing everything during COVID, and why sometimes you have to shut successful doors to open bigger dreams. I share my "superpowers" of community building and organization, how prayer guided my pivot decisions, and the vision for taking The Brighter Side Society worldwide while building The Holmestead Bar & Retreat in the Caribbean.

Whether you're a female entrepreneur feeling pulled in multiple directions, considering a major business pivot, or ready to turn overwhelming dreams into organized action, this episode offers both vulnerable storytelling and practical business strategies. This is the "B" in BIGGIE—Believe—in your bigger vision even when it means closing chapters you love.

Instagram

@thebrightersidesociety and @angelpholmes

Learn More

👩‍💼 The Brighter Side Society

📧 Email: angel@neverstopdreamingbiggie.com

🌐 Website: sipindipity.com

Takeaways

• Discover how to identify your core business superpowers and lean into them
• Learn when to close profitable ventures to pursue your bigger purpose
• Master community building by focusing on connection before monetization
• Create systems and organization to turn overwhelming dreams into action
• Navigate major business pivots with faith and strategic planning
• Transform COVID setbacks into comeback stories through purpose-driven decisions
• Scale from local impact to global reach through authentic storytelling
• Balance entrepreneurial creativity with practical implementation
• Recognize when you're spreading yourself too thin across multiple ventures
• Use prayer and reflection to guide life-changing business decisions

Chapters

00:00 Welcome & Life Changes Announcement

02:15 Angel's Career Background & Journalism Roots

05:30 World Cup Internship That Changed Everything

08:45 The Birth of Charleston Wine & Food Festival

15:20 Building a 6-Figure PR Business Empire

22:10 COVID Setbacks & Rock Bottom Moments

28:35 Reading "Purpose Driven Life" & Finding Direction

35:40 Creating Like Minded Charleston Community

42:15 The Brighter Side Society Vision Goes Global

48:30 Making the Difficult Decision to Close Like Minded

52:20 Future Plans: The Holmestead & Caribbean Dreams

56:45 How to Join The Brighter Side Society

59:30 Faith, Purpose & Next Steps