Dawn Fleming

Managing Director @ eWomenNetwork

About

You’ve built success. A career. A reputation. A life that works. And now there’s a different question. Not “What else do I need to prove?” But “What do I want this next chapter to stand for?” Midlife was never meant to be a slow transition into retirement. It’s a moment of design. A point where you have the experience, perspective, and awareness to choose more intentionally—how you live, how you spend your time, and what truly matters now. My own turning point came in my 50s. After a financial collapse, my husband and I sold everything, sailed from California to Florida through the Panama Canal, and rebuilt our lives from scratch on a small island in Mexico. Not because we had to. Because we saw what was possible. Today, through Life in Paradise, I work with accomplished women who are no longer interested in drifting into the next chapter by default. Women who are ready for: More freedom—not just financially, but in how they live More meaning—beyond roles, titles, and expectations More intentional design—of their time, energy, and life This isn’t about starting over. It’s about stepping into the most aligned, expansive version of what comes next. Midlife is not a wind-down. It’s where you decide how you want to live—with clarity, choice, and purpose.

Country

City

Mexico

Industry

Media Production

Skill

Business Matchmaking, Business Relationship Management, Mastermind Facilitation, Professional Networking, Problem Solving, Business Strategy, Public Speaking, Entity Formation, Small Business, Entrepreneur, Business Planning, Business Networking, Marketing, Sales Management, Entrepreneurship, Personal Development, Social Media, Public Relations, Real Estate, Strategy

Experience

Managing Director

eWomenNetwork

2025-10 - Present · 1 yr

Mexico

I'm Managing Director of the FIRST eWomenNetwork Chapter in Mexico. This is in coordination with my current businesses, not in place of them. I'm building this new community alongside what I already do because I know what's possible when women business owners connect strategically. What I see: - Brilliant women building incredible businesses... completely alone. - Making tough decisions without a sounding board. - Celebrating wins without the support of those who really get it. - Missed opportunities because they lack the right connections. - Reinventing wheels that someone else has already figured out. - Wondering if they're the only one struggling to finding a community of thriving women business owners What I know: * We're NOT supposed to be doing this alone. * The most successful women entrepreneurs don't build in isolation. * They have people to call when a deal falls through. * They have strategic partners who refer them real business. * They have mentors who've walked the path before them. The eWN philosophy that deeply resonates? "Give First, Share Always." I'm launching: ✨ A community where collaboration beats competition ✨ Access to proven strategies from women who've already scaled successfully ✨ Real opportunities, not stacks of business cards ✨ Cross-industry connections that miraculously open doors ✨ A culture of abundance where your success breeds more success for everyone ✨ Events designed to actually move your business forward I'm sharing: * How successful women entrepreneurs actually build revenue * The power of strategic relationship building * What "lifting others as we climb" looks like in practice * Behind-the-scenes of creating a business community that works * Opportunities to connect before the official launch in Mexico * How you can benefit even if you aren't in Mexico It's just the beginning. If you're a woman business owner who's ready to stop building alone, let's have a conversation. I'm here to help.

Host @midlifeinparadise YouTube Channel

Life in Paradise

2024-5 - Present · 2 yrs 5 mos

Chick in Charge

Castillito Del Caribe

2018-1 - Present · 8 yrs 9 mos

Isla Mujeres, Quintana Roo, Mexico

Castillito del Caribe is a fabulous vacation rental home in a perfect location on the magical Caribbean island of Isla Mujeres. Check out our Awesome Villa in a Perfect Location! https://castillitocaribe.com