Using the Enneagram to:
Cultivate deeper self-awareness
Gain better understanding of others
Develop new habits & practices for growth
Experience freedom through a transforming life

One guiding question through my life has been “what does it take to make this a thriving space?” Whether it’s the community where I live, the church that I attend, or my inner world and home. I am driven by the desire to bring life-giving practices and opportunities to our world.

I believe the more we know ourselves and bring self-leadership to the spaces we inhabit, the greater potential for positive change and transformation. I have experienced this in my marriage and in many relationships. Author and psychologist David Benner has said: “You cannot change what you cannot name.” If we want to change our unhealthy patterns of how we react to ourselves and others, we have to do the inner work of noticing, naming, and turning from those patterns. What I love about the Enneagram is that it not only shows us our struggles, but our opportunities for growth as well.

I studied history and urban planning, and have worked for community nonprofits and collaborations, ministries, and for-profit businesses over the last decade (plus!).

I received my Bachelor’s in History from Florida State University and my Master’s in Urban and Environmental Planning from the University of Virgina. In 2021 I completed the Transforming Center Community Experience and received my certificate in Spiritual Transformation. In Spring 2021 I completed my Enneagram Training through YEC and continue my professional development through readings and teachings of several prominent teachers.

I currently call Florida home and am a wife, mom of 2 boys, and leader of a Safe Families for Children chapter.


I would highly recommend Jessie Ray for your enneagram work for your leadership team. She worked with our team to explain basics about the enneagram and gave us a simple understanding about how to grow emotionally and why it is important to keep growing. Then we received information on how we could work better and smarter as a team as we think about how each person has been created and therefore how they hear things, process, interact with their world, like to hear criticism, and work together.
~Director, International Nonprofit
Jessie Ray is a clear and powerful presenter. Skillfully combining in depth understanding of the Enneagram and spiritual formation she provides a balanced and nuanced approach to her training. ~Nonprofit ministry team member
Hybrid, Virtual, In-Person
Individual, Group, Couple, Workshop
Monday, Tuesday, Wednesday, Thursday, Friday


Certified Enneagram Coach
Certificate in Spiritual Transformation
Transforming Center Community 15