meet cynthia

As an executive life coach and life strategist, I have spent more than a decade helping people find their “happy.” My work is rooted in my experience as a writer and published author — I have a keen sense of “the story” we all tell about our lives. My goal is to help my clients change their narrative from “I can’t” and “I’m afraid” to “I am willing to see this in a new way and tell a different story.” I help mid-career executives, small business owners, and would-be authors achieve the life they crave.

I am a certified coach through the  International Coaching Federation and past board member for the International Coaching Federation, Bay Area Chapter. 

twenty+ years of nonprofit leadership

Previously to my work as an executive life coach, I held leadership roles with large and small nonprofit teams, managed boards of directors, and helped raise more than $20M. I was the Director of Annual Giving at Alta Bates Summit Foundation, the VP of Development at St. Andrew Legal Clinic, Executive Director at Clinic Ole Foundation, Foundation Officer at Novato Community Hospital, and Director of Philanthropy, at Elder Care Alliance. I am a member of the Association of Fundraising Professionals.

With an MFA in Creative Writing from Mills College, I am an award winning writer and author of Journaling As Sacred Practice: An Act of Extreme Bravery and What is Possible From Here. I am also a member of the California Writers Club.

I live in the beautiful community of Sonoma, California. In my spare time, I love to hike,  walk my rescue pups, Winston and Blue, travel, and prepare gourmet meals for friends. 

I invite you to learn more about my background on LinkedIn.

testimonials for cynthia

In 2019/2020 I had the privilege of participating in a Mastermind Circle with several non-profit leaders, led by Cynthia Gregory. The MM meetings began as an exchange about the challenges of managing our organizations and to some extent, our personal lives. Coach Cynthia structured the meetings around thought-provoking questions and discussions that helped develop the circle into safe place for sharing ideas, advice and lots of laughter. The highlight was hearing how my fellow ED’s had solved a problem, established a partnership, obtained a long-sought after grant, recruited a hard to fill position, etc. and acknowledging these wins. The fact that we have remained friends and continue to meet monthly, albeit informally, is a testimony to the power of the experience. I highly recommend it.

Rebecca B. | Napa, CA

“Cynthia is an exceptional coach! Her curiosity and ability to meet me where I was currently at established safety and trust. She asks great questions and I was able to look deeper, gain clarity about my issues, and see what actions I could take. I felt fully supported and empowered with Cynthia. And she makes the journey fun! I highly recommend Cynthia to everyone!!”

Leonie D. |Los Angeles, CA

“We retained Cynthia to moderate our annual Strategic Planning meeting with our group of 9 employees. Cynthia arranged an efficient interactive agenda with a perfect balance of open discussion, team-building and self-reflection. It was a positive, productive day, setting the stage for the rest of the 2019.”

Rebecca B. | Napa, CA

“Cynthia Gregory is sharp and wise with a complete library of success architect tools to help you up-level your life! She listens and offers concrete effective strategies to assist you in accomplishing your goals, be it professional goals or personal goals. She is, and continues to be, an amazing coach.”

Candice Y. | San Rafael, CA

“Cynthia is an amazing coach! She has helped me both personally and professionally set goals for myself and then actually achieve those goals. I look forward to our sessions because I know I will put something significant into action every time, and the energy we have built up keeps me motivated toward success.”

Dawn D. | San Rafael, CA

ready to get started?

Schedule a free Discovery Coaching Session at:   
Phone: (503) 360-6570

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