We were lucky to catch up with Cindy Morgan-Jaffe recently and have shared our conversation below.

Hi Cindy, thanks for joining us today. One of the toughest things about progressing in your career is that there are almost always unexpected problems that come up – problems that you often can’t read about in advance, can’t prepare for, etc. Have you had such and experience and if so, can you tell us the story of one of those unexpected problems you’ve encountered?

The unexpected challenge I faced as a dedicated and passionate entrepreneur was underestimating the power of money mindset. By age 40, after building several businesses but struggling to truly thrive, I recognized that a lifetime of unconscious beliefs and behaviors around money was holding me back from the success I envisioned. This realization led me to develop the 7 Principles of Positive Money and write my book, which now serves as the foundation for the Positive Money Club—a supportive community helping women 50+ get financially fit and align their money with what matters most.

Cindy, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?

I’m the founder of the Positive Money Club and Gym, a community for women 50+ to get “money fit” and align their finances with what matters most. The work grew out of my own story—a pivotal moment in my early 50s when I realized my relationship with money was quietly sabotaging my dreams.

One sleepless night, after yet another conversation with my wife about my frustration running a startup on a shoestring budget, I felt stuck. I had built businesses before, worked in the nonprofit sector, and raised five kids through two marriages—but I was haunted by the same question: Was I ever going to feel confident and secure with money, or would fear and self-doubt keep holding me back?

That night became a turning point. I discovered the field of financial therapy and began unraveling my own limiting beliefs about money. This journey led me to create the 7 Principles of Positive Money, write a book, and launch the Positive Money Club.

Today, I help mission-driven women in midlife build clarity, confidence, and commitment around their finances—not just for their own peace of mind but to create legacies they’re proud of. What sets my work apart is the focus on financial wellness as both a practical and emotional journey. It’s not about spreadsheets or shame; it’s about empowering women to take charge of their money in a way that feels aligned, intentional, and doable.

While these questions rolled across my mind like a ticker tape, I wondered how I could move forward and realize my dream if I was paralyzed by fear and self-doubt. That’s when it hit me. I was expecting to fail. Even worse, I was expecting someone to save me when I did.

The above story was a pivotal. It was when I discovered the field of financial therapy and money mindset, and how so many of us struggle to take care of our money so that it can take care of us.

It also led me to write a book and to work with women 50+ who want to get money fit by building confidence, clarity, and commitment to their financial lives, not just for themselves but for those they love most.

Can you share a story from your journey that illustrates your resilience?

Finding grace in life’s messiness has taught me that a rich life is always available—as long as we’re willing to show up for it. I’ve always been a seeker, often chasing greener grass, but it’s the hard seasons that shaped me most.

After a year living in Rome as an art director for a children’s fashion magazine, I returned to the U.S., married a journalist, and ran a thriving freelance design business while raising three daughters. But in my early forties, everything shifted. I earned a master’s in education and human development, changed careers, fell in love with a woman, and navigated a painful divorce. It was a time of deep disruption and self-discovery as I rebuilt my life and sense of identity.

Over time, I came to understand how vital self-love and self-worth are to living richly. My wife and I later welcomed twins, blending our family of five children while building separate careers and businesses. It wasn’t easy, but it taught me that resilience isn’t about avoiding the storms—it’s about learning to dance in the rain.

Through it all, I realized how profoundly our relationship with money shapes our ability to navigate life’s big transitions. If we rely on others to manage it, what happens when we’re suddenly on our own? If we avoid money conversations, what opportunities are we missing? And if we think a rich life requires “more,” what does enough really look like? These are the questions that inspired the Positive Money Club and continue to guide my work today.

Where do you think you get most of your clients from?

The best source of new clients has been my network—relationships I’ve nurtured personally and professionally over the years. I’ve always known the power of building trust and connection, but it became even clearer after raising a family and coming up for air. I realized my clients are women like me—navigating transitions, seeking meaning, and wanting a richer life that isn’t defined by a bank balance.

By sharing my own challenges and committing to creating a safe, judgment-free space, I’ve been able to attract women who resonate with the Positive Money philosophy. They’re not chasing a magic number; they’re ready to build confidence, clarity, and alignment around their money so it can take care of what matters most.

Contact Info:

• Website: https://www.positivemoneyclub.com/
• Instagram: https://www.instagram.com/positivemoneyclub/
• Facebook: https://www.facebook.com/cindy.morganjaffe/
• Linkedin: https://www.linkedin.com/in/morganjaffe/

Image Credits

Rose Jaffe (Cindy with Pup) John Morgan photographer of Cindy skiing