loader from loading.io

How to Lead with Courage and Vulnerability, feat. Dr. Terence Lester (Enneagram 8)

Typology

Release Date: 09/04/2025

The Art of Listening: An Eight Step Approach to Connection with Emily Kasriel show art The Art of Listening: An Eight Step Approach to Connection with Emily Kasriel

Typology

This week, we explore the art of listening and the complexities of human personality through the lens of the Enneagram with Emily Kasriel, an award-winning journalist, executive coach, and author of the new book, Deep Listening: Transform Your Relationships with Family, Friends, and Foes. Emily shares her journey of self-awareness and the importance of deep listening in our everyday interactions. She discusses her experiences at the BBC, the challenges of listening in high-stakes situations, and the powerful eight-step approach to deep listening outlined in her book. Discover how to...

info_outline
How to Lead with Courage and Vulnerability, feat. Dr. Terence Lester (Enneagram 8) show art How to Lead with Courage and Vulnerability, feat. Dr. Terence Lester (Enneagram 8)

Typology

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...

info_outline
1,000 Hours Outside: Rediscovering the Freedom of Play with Ginny Yurich show art 1,000 Hours Outside: Rediscovering the Freedom of Play with Ginny Yurich

Typology

This week on Typology, I sit down with Ginny Yurich—author of Until the Streetlights Come On and Homeschooling: You’re Doing It Right Just by Doing It. Together, we revisit the freedom of childhood play, explore how modern parenting has shifted, and talk about why kids today desperately need more time outdoors. Ginny, an Enneagram Two, shares candidly about her own parenting journey—what she’s learned about boundaries, mutuality, and the deep desire to feel appreciated. She also introduces her initiative, 1,000 Hours Outside, which is inspiring families around the world to reclaim the...

info_outline
The ADD Method for Emotional Freedom with Enneagram One, Alicia Michelle show art The ADD Method for Emotional Freedom with Enneagram One, Alicia Michelle

Typology

In this episode of Typology, I sit down with Alicia Michelle—an Enneagram One and host of The Christian Mindset Coach podcast—for a meaningful conversation about emotions, perfectionism, and the journey toward self-compassion. Alicia shares her story of discovering her true type, the freedom that comes from quieting the inner critic, and her practical ADD method (Acknowledge, Discern, Decide) for processing emotions. Together, we explore the importance of emotional literacy, how different types experience emotions, and why learning to govern our inner world is key to growth. Whether...

info_outline
Building an Emotionally Healthy Family in a Culture That Won’t Stop Shouting, with Sarah Boyd, M.Ed. in Psych show art Building an Emotionally Healthy Family in a Culture That Won’t Stop Shouting, with Sarah Boyd, M.Ed. in Psych

Typology

Ever feel like the world’s volume knob is stuck on “too loud”? In this week’s episode of Typology, I’m joined by my friend Sarah Boyd—an insightful Enneagram Four and author of the brand-new book, . Sarah has walked through seasons of deep beauty and deep challenge—including her own cancer journey—and she’s here to share how those experiences have shaped her understanding of creativity, meaning, and the role our emotions play in living a full, authentic life. We talk about how overstimulation impacts both adults and kids, why recognizing our limitations matters, and how...

info_outline
From VeggieTales to the Enneagram: Mike Nawrocki on Peace, Presence, and Purpose show art From VeggieTales to the Enneagram: Mike Nawrocki on Peace, Presence, and Purpose

Typology

What happens when a peace-seeking Enneagram Nine becomes the voice of one of the most beloved animated characters in children’s television? Find out as we dive into the world of the Enneagram with special guest Mike Nawrocki, co-creator of VeggieTales and the voice of Larry the Cucumber. In this engaging conversation, we explore the unique traits of Enneagram Nines, known as the Peacemakers. Mike shares insights from his journey in creating beloved children's content, including his latest project, The Dead Sea Squirrels, which is now a growing book series and animated show. We discuss the...

info_outline
Understanding Enneagram Twos: Desire, Boundaries, and Connection with Emily Zeller, LMFT show art Understanding Enneagram Twos: Desire, Boundaries, and Connection with Emily Zeller, LMFT

Typology

What happens when your deep longing to love and be loved gets tangled up with your need to be needed? In this week’s episode of Typology, Anthony and I sit down with the wonderful Emily Zeller—a licensed marriage and family therapist, certified Enneagram practitioner, and a one-to-one Enneagram Two. Emily brings such honesty and heart as we talk about desire, boundaries, and the tender places in all of us that crave connection. As we explore the unique energy of the Enneagram Two and unpack the three subtypes—self-preservation, social, and one-to-one—we ask questions we can all sit...

info_outline
A Change of Habit: Sister Monica Clare's Journey from Advertising to Nunhood show art A Change of Habit: Sister Monica Clare's Journey from Advertising to Nunhood

Typology

Welcome to this enlightening episode of Typology! Join us as we explore the life and journey of Sister Monica Clare, an Enneagram 6 and author of the memoir A Change of Habit: Leaving Behind My Husband, Career, and Everything I Owned to Become a Nun. In this episode, we explore: Sister Monica's experiences growing up in a chaotic environment and how it shaped her Enneagram type. The unique challenges and joys of being an Enneagram 6 in a religious community. The intersection of spirituality and personality, and how the Enneagram informs her spiritual practices. Insights from her...

info_outline
Desire, Longing and the Enneagram, feat. Tracey Gee show art Desire, Longing and the Enneagram, feat. Tracey Gee

Typology

In this episode of Typology, we welcome Tracey Gee, an Enneagram 3w2 and author of the new book, The Magic of Knowing What You Want: A Practical Guide to Unearthing the Wisdom of Your Desires. Tracey shares her journey of discovering the Enneagram in her late 20s while navigating the challenges of vocational ministry and familial expectations. She reflects on how understanding her Enneagram type has transformed her approach to life, particularly in recognizing the difference between societal scripts and her authentic desires. We dive into the nuances of desire, want, and longing,...

info_outline
Taming Your Money Monster: Understanding Finances Through the Lens of the Enneagram, feat. Doug Lynam show art Taming Your Money Monster: Understanding Finances Through the Lens of the Enneagram, feat. Doug Lynam

Typology

In this episode of Typology, we welcome Doug Lynam, an Enneagram 3w4 and author of the new book "Taming Your Money Monster: Nine Paths to Money Mastery with the Enneagram." Doug shares his fascinating journey from Marine Corps officer to Benedictine monk and now money manager, exploring how the Enneagram can provide insights into our relationship with money.  Join us as we dive into the unique "money monsters" associated with each Enneagram type, discussing how childhood narratives shape our financial behaviors and the importance of authenticity in achieving a healthier relationship with...

info_outline
 
More Episodes

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.