How to Lead with Courage and Vulnerability, feat. Dr. Terence Lester (Enneagram 8)
Release Date: 09/04/2025
Courageous Conversations: How Your Conflict Style Shapes Every Difficult Conversation
Typology
What if the conversations you’re avoiding… are actually the doorway to the relationships you want? In this replay from our Courageous Conversations series, I sit down with conflict resolution expert James Guinn to explore a truth most of us would rather sidestep: conflict isn’t the problem—our style of engaging it is. Together, we unpack the hidden patterns that shape how you show up when tension rises—whether you withdraw, accommodate, compete, analyze, or collaborate—and how those instincts, often wired beneath your awareness, quietly drive the outcomes of your hardest...
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Courageous Conversations: Why We Struggle to Ask for What We Want (and How to Change It) with Attia Qureshi
Typology
Last week, we kicked off our Courageous Conversations series with a fresh look at building emotional confidence. This week, we lay the groundwork for how personality, emotional regulation, and awareness all play into navigating conversations that matter. I sat down with Attia Qureshi—an expert in negotiation and persuasion—but what unfolds isn’t just about getting what you want. It’s about why we want what we want…and what’s really driving us underneath it all. Attia shares a moment of deep rejection from her childhood that led her to build what she calls an “exoskeleton”...
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Courageous Conversations: The Inner Work that Builds Confidence
Typology
This week, we're kicking off a multi-week series on how to have courageous conversations. We'll be digging into the foundations of emotional confidence, strategies for negotiation, and how to have difficult conversations. Today, we’re taking a fresh look at our conversation with Alicia Michelle to learn how to slow down your inner world and regulate your thoughts, your emotions, and your reactions before you ever step into a hard conversation. We’re talking about building emotional confidence. Not the loud, chest-thumping kind. I mean the quiet, grounded ability to...
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Replay: When the Life You Built Breaks Open w/Jen Hatmaker
Typology
What happens when the life you built—carefully, faithfully, and very publicly—splits down the middle in a single night? This week on Typology, we’re revisiting one of the most powerful conversations we’ve had on the show—a replay of my interview with bestselling author and cultural truth-teller Jen Hatmaker. Jen, an Enneagram Three with a courageous edge that sometimes looks a lot like an Eight, joined me to talk about her memoir Awake and the “before-and-after date” that changed everything—July 11, 2020— when her 26-year marriage ended and the life she knew cracked wide...
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Feeling Different? A Deep Dive into the Enneagram 4 Experience with Dudley Delffs
Typology
There are some conversations that don’t just inform you—they find you. This was one of those for me. In this episode, I sit down with my friend Dudley Delffs—author, therapist, and a fellow self-preservation Four—and what unfolds is less of an interview and more of an honest, unguarded conversation between two people who’ve spent a lifetime trying to tell the truth about their lives…and sometimes wondering what it costs to do that. We talk about the long journey of being a Four—the early years of feeling different, the instinct to hide parts of your story, and the slow, sometimes...
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How the Enneagram Transforms Leadership and Workplace Culture
Typology
Most leaders think workplace problems are about strategy, performance, or communication. But what if the real issue is something deeper—something invisible shaping how people interpret everything that happens at work? In this episode of Typology, Anthony and I explore how the Enneagram reveals the hidden motivations driving behavior inside teams and leadership groups. When people begin to understand why they—and their colleagues—think, react, and communicate the way they do, everything starts to shift. We talk about what happens when organizations move beyond personality labels and start...
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Part 2: The Enneagram in Therapy (What It Looks Like in the Room)
Typology
In Part 2 of our conversation on using the Enneagram in therapy, we move from theory to lived experience in the room. Anthony and I discuss how type can be understood as an adaptive survival strategy shaped by early attachment and trauma—and how that framing reduces shame instead of reinforcing it. We talk about what it looks like when the Enneagram is actually working in session: increased self-observation, greater emotional regulation, and more compassion. As a therapist, your type doesn't clock out when the session starts, so we dig into the importance of self-awareness and...
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The Enneagram in Therapy (Part 1): How to Use It With Care, Clarity, and Clinical Wisdom
Typology
What does it mean to use the Enneagram in therapy responsibly? In Part 1 of this two-part conversation on Typology, Anthony Skinner and I lay the groundwork for therapists, counselors, and coaches who want to responsibly integrate the Enneagram into clinical practice with wisdom and care. Together, we unpack what the Enneagram is—and what it isn’t—in the therapy room. It’s not a diagnosis. It’s not a substitute for evidence-based modalities. And it should never flatten complexity or bypass deeper trauma work. I also share practical wisdom from decades of work as a therapist,...
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The Future of Mental Health: Psychedelics, Trauma Recovery, and the Enneagram
Typology
There are conversations that stretch you a little. And then there are conversations that gently but firmly rearrange the furniture in your mind. This week, I sat down with Keith Kurlander and Will Van Derveer—co-founders of the Integrative Psychiatry Institute—to talk about something that’s generating a lot of curiosity and, let’s be honest, some anxiety: psychedelic-assisted therapy. Before you brace yourself, this isn’t a hype session. It’s a thoughtful, grounded conversation about trauma, the nervous system, and what happens when traditional therapy isn’t enough to reach the...
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When Therapy Speak Goes Too Far, with Joe Nucci
Typology
In this episode of Typology, I sit down with therapist and author Joe Nucci for a thoughtful, wide-ranging conversation about the Enneagram, mental health, and the growing misuse of therapeutic language in our culture. Joe—an Enneagram Three—shares his own journey with the Enneagram, the hidden shame dynamics of Threes, and how public success can quietly pull us toward performance instead of integrity. Together, we explore why tools like the Enneagram work best as maps, not MRIs—helpful for self-awareness and empathy, but dangerous when they turn into rigid labels. We also dig into...
info_outlineIn 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.