In this week’s episode of Typology, I sit down with Dr. Terence Lester—an Enneagram Eight, author of From Dropout to Doctorate, and the visionary founder of Love Beyond Walls. Terence’s story is as powerful as it is inspiring. From his early years in Atlanta to leading a movement that uplifts those experiencing poverty and homelessness, his journey embodies both courage and compassion.

Together, we explore what it means to be an Enneagram Eight in the trenches of community work—wrestling with control, burnout, and the temptation to over-function. Terence opens up about a devastating car accident that reshaped his sense of identity, his relationship with productivity, and ultimately, his capacity for gratitude.

We also dive into the intersection of action and contemplation, the influence of Henri Nouwen on Terence’s life, and the healing power of reconciliation in his own family story. Along the way, Terence reminds us that leadership isn’t about posturing but about vulnerability, presence, and the willingness to walk alongside others in their pain.

This conversation is an invitation to rethink how we serve, how we love, and how we grow. You’ll walk away with profound insights about resilience, healing, and the transformative power of the Enneagram.

ABOUT OUR GUEST

Dr. Terence Lester is a storyteller, public scholar, speaker, community activist and author of From Dropout to Doctorate. He is the founder and executive director of Love Beyond Walls, a nonprofit organization focused on raising awareness about poverty, homelessness and community mobilization. He serves as the director of public policy and social change and as a professor at Simmons College of Kentucky (HBCU). He received his PhD with a concentration in public policy and social change from Union Institute and University. Terence has authored four additional books with IVP, including one with his sixteen-year-old daughter, Zion, titled Zion Learns to See: Opening Our Eyes to Homelessness. The other titles include I See You: How Love Opens Our Eyes to Invisible People, When We Stand: The Power of Seeking Justice Together, and All God’s Children: How Confronting Buried History Can Build Racial Solidarity.

Terence is known for nationwide campaigns that bring awareness to homelessness, poverty and economic inequality. His awareness campaigns have been featured on ML K50, CNN, Good Morning America, Essence, TEDx, TVONE, Creative Mornings, USA Today, NBC News, Black Enterprise, Rolling Out, Upworthy and more. These campaigns have been viewed by millions of people worldwide. Terence is happily married to his best friend, Cecilia, and they have two amazing children, Zion Joy and Terence II.

Learn more about Dr. Lester by visiting his website at www.terencelester.org or follow on social media at @imterencelester or @lovebeyondwalls.

Dee Giallo Story - Chet Baker (2016)