Afleveringen
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We're going back into the vault for one of our most popular mailbag episodes from Season 3 — and the questions are just as good as we remembered.
In this episode, Ian and co-host Anthony Skinner answer listener questions on some of the Enneagram's most nuanced and personal territory: Can trauma actually change your type? What is the "sunny Four," and why do subtypes matter so much for Fours and Sixes? How do Threes and Fours process grief differently — and what does healthy grieving even look like through an Enneagram lens? What does it mean to have a heavy wing, and can you access both wings for growth? And for the Ones in the room — what do you actually do with all that repressed anger?
Whether you're new to Typology or you've been with us for years, this one is worth your time.
Have a question of your own? Send it to [email protected] and you might hear it answered on our next mailbag episode.
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What if the reason your closest relationships feel stuck isn't about how much you care — but about how differently you and the people you love communicate? Today, I sit down with Jason VanRuler, therapist, Enneagram Two, and author of Discovering Your Communication Type: The 5 Paths to Deeper Connection and Stronger Relationships, as he introduces us to his P.A.T.H.S. framework — five communication styles he identified through years of working with couples navigating betrayal, teams in conflict, and individuals trying to understand why the same words land so differently depending on who's in the room. Those five types: the Peacemaker, the Advocate, the Thinker, the Harbor, and the Spark.
The nine Enneagram types map fascinatingly onto these five communication styles, and we walk through each type together. We talk about blind spots (every communication style has one), what happens to our style under stress and in conflict, and why the most generous thing you can do in any relationship is learn to speak your people's language rather than demanding they speak yours.
Jason also shares honestly from his own marriage — he's a Harbor married to a Thinker — and what changed when he learned to stop reading his wife's precision questions as opposition and started hearing them as her version of love.
Whether you're an Enneagram enthusiast, a couples therapist, a team leader, or just someone who's tired of feeling unseen in conversations, this episode is for you.
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Zijn er afleveringen die ontbreken?
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What if the very thing driving your success is quietly breaking you?
Brooke Taylor, Enneagram Three, career coach, and author of Healing the Success Wound, joins me for a searingly honest conversation about achievement, identity, and spiritual hunger.. Brooke grew up in Silicon Valley where worth was measured in gold stars, landed at Google by her early twenties, and found herself drowning in a success she couldn't feel. We talk about the success wound which, as Brooke describes it, is the pain that comes from mistaking productivity and achievement for self-worth — the deeply installed belief that the more you produce and achieve, the more worthy of love and belonging you become.
This wound isn't just for Enneagram Threes. It's a human condition — and it shows up differently depending on your type, your culture, your family system, and what "success" looks like in your particular world.
We talk through Brooke's five types of unfulfilled achievers — the grinder, the hider, the seeker, the work-hard-play-hard, and the pleaser — and I couldn't help mapping those to the Enneagram types in real time. We also get into the distinction between the true self, the wounded self, and the socialized (or protector) self — a framework rooted in Internal Family Systems and gestalt psychology that I think will resonate deeply with longtime Typology listeners.
Whether you're a Three or you love one, this episode is for you.
Guest Bio:
Brooke Taylor is a certified career coach, speaker, and the author of Healing the Success Wound. A self-identified Enneagram Three, Brooke built her coaching practice specifically for women navigating the intersection of ambition, identity, and fulfillment — though her framework applies broadly across genders. Her research includes a survey of more than 5,000 high-achieving professionals who identified as unfulfilled, which forms the empirical backbone of her five-type model of the unfulfilled achiever. A veteran of Google and a long-term member of recovery communities, Brooke brings both lived experience and rigorous research to her work. She is the founder of the Lined Ambition framework and writes and coaches at the crossroads of psychology, spirituality, and career development. Learn more at brooketaylor.co.
Healing the Success Wound is available now wherever books are sold.
Find Brooke at https://brooketaylorcoaching.com.
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Have you ever known where you want to go—but felt mysteriously stuck getting there? In this episode of Typology, I sit down with Dr. Henry Cloud, clinical psychologist, leadership expert, and bestselling author of Boundaries, to talk about his new book, Your Desired Future: The Five Essential Steps That Take You Where You Want to Go.
Together, we explore the intersection of faith, psychology, the Enneagram, self-awareness, and personal growth, and how real transformation begins when we stop shaming ourselves for where we are and start getting curious about what's possible. Henry brings his characteristic wisdom, warmth, and clinical insight to a conversation about healing, purpose, emotional health, and the practical path from "here" to "there."
This is a thoughtful and hope-filled conversation for anyone who feels stuck, is navigating change, or wants to better understand the patterns that shape the life they're living.
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"Emotions drive 90 to 95% of our unconscious decision-making."
Attia Qureshi is back — and this time, we go deeper.
After her first interview, Attia's insights on persuasion and negotiation were so helpful that Anthony put them to the test in a real-life negotiation and said, "they changed the game." So, we invited her back to go deeper into the ideas behind her book, Never Settle: Persuasion and Negotiation Skills to Get What You Want, and explore how each Enneagram type approaches one of the most important conversations we can have: asking for what we need.But, as Attia explains, negotiation isn't just something that happens across a boardroom table. It happens every day – with our spouses, our kids, our coworkers, our neighbors, and perhaps most importantly, within ourselves. Before we ever make an ask, we have to face the internal stories, emotions, fears, and assumptions that often keep us from speaking up in the first place.
In this episode, we explore how different Enneagram types navigate negotiation, conflict, emotional regulation, self-advocacy, and the art of creating value without damaging relationships. We unpack why some types avoid the ask, why others over-assert, why some need more clarity around what they actually want, and how every type can grow in confidence, courage, and self-awareness.
You'll learn:
How emotions shape the way we ask – or don't ask – for what we need
How to identify and label your emotions so they stop driving your decisions unconsciously
The worst-case scenario exercise that builds resilience and inoculates you against fear
What each Enneagram type brings to the negotiation table — where they shine, where they get stuck, and what to do about it
A breathing technique that signals your nervous system it's safe before a high-stakes conversation
You can learn more about Attia and grab her free resource for Typology listeners, which includes a breakdown of each Enneagram type's negotiation strengths, blind spots, and exercises at https://attiaqureshi.com/typology.Never Settle: Persuasion and Negotiation Skills to Get What You Want by Attia Qureshi and John Richardson is available now wherever books are sold.
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Every once in a while, a conversation comes along that makes you pull out your earbuds and stare into the middle distance. This is one of those.
My guest today didn't come to promote a book or launch a course. He's here because he's a good friend with hard-won wisdom — and the rare ability to articulate what's actually going on inside. Meet Brian Boecker, therapist at Restoring the Soul in Denver, Colorado, and an Enneagram Nine who has spent years doing the slow, unglamorous, profoundly important work of finding himself.
We go deep on what it really means to belong versus simply fit in, why desire is so terrifying to name out loud, and how anger — when you stop running from it — turns out to be something closer to a life force than a liability. Brian is disarmingly honest about the ways he's learned to disappear, the slow work of becoming solid, and what it looks like to finally walk through the door you've been standing in front of your whole life.
Whether you're a Nine or you love one, this conversation will give you a richer, more compassionate picture of what's actually going on beneath that calm surface.
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What happens when two powerful paths—Buddhism and the Enneagram—sit down for a conversation?
In this episode, Ian welcomes author and Buddhist teacher Susan Piver (The Buddhist Enneagram) to explore the overlap between these two systems. Susan's new book, The Buddhist Enneagram, offers a fresh lens on personality—not as something to fix, but as something to understand, soften, and ultimately hold with compassion.
This conversation goes beyond personality labels and into something deeper: How your patterns form, why they stick, and how awareness—not willpower—is what actually creates change.
If you've ever felt stuck in your reactions, overwhelmed by your emotions, or quietly convinced you're "doing life wrong," this episode offers a different path forward.
Together, they unpack:
How the Enneagram and Buddhism overlap (and where they challenge each other)
The difference between mindfulness and awareness (and why both matter)
How meditation helps you notice your reactions without being ruled by them
Why trying to "fix yourself" often backfires—and what works instead
How Enneagram subtypes shape conflict, connection, and relationships
As always, this isn't about becoming someone else. It's about becoming more fully who you already are—with a little more grace along the way.
About Susan PiverSusan Piver is a Buddhist teacher, meditation instructor, and author of The Buddhist Enneagram. Her work bridges ancient wisdom and modern psychology, helping people cultivate compassion and awareness in everyday life.
Subscribe & FollowIf this episode resonates, follow the show so you don't miss future conversations on the Enneagram, relationships, and spiritual growth.
Share This EpisodeKnow someone who's deep into the Enneagram—or stuck in their patterns? Send this their way. It might be exactly what they need to hear.
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Most of us think we're avoiding hard conversations because we don't know what to say.
But that's not really the problem.
In this episode, Ian and Anthony dive into the real reason we sidestep the conversations that matter most—and it has a lot less to do with skill and a lot more to do with what's happening inside of us.
Because here's the truth: you can have the best negotiation strategy in the world, but if you don't understand the emotional dynamics underneath the conversation, you're going to be dead in the water.
As part of our Courageous Conversations series, this episode serves as the emotional intelligence companion to negotiation—helping you move from avoidance to clarity, from anxiety to grounded confidence.
Ian unpacks:
Why we were never taught how to have hard conversations (and what we learned instead)
The "fool's choice" that keeps us stuck between silence and relational fallout
How the stories we tell ourselves quietly shape our emotions and reactions
The three common narratives (victim, villain, helpless) that sabotage connection
A simple but powerful 5-step framework to actually have the conversation
What to do when things go sideways—and how to restore safety in real time
Along the way, you'll discover that the goal isn't just to "say it better"—it's to show up differently.
Because hard conversations don't ruin relationships. Avoiding them does.
So as you listen to this episode, ask yourself: "What's one conversation you've been avoiding—and what would it look like to walk into it just a little more prepared?"
**This episode is part of our ongoing Courageous Conversations series—where we're learning how to speak honestly, navigate tension, and build stronger, more trust-filled relationships in the places that matter most.
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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 conversations.
Here's the deal: every difficult conversation is a negotiation. Not just of outcomes, but of needs, emotions, and meaning. And if you don't understand your default conflict style—or the style of the person across from you—you'll keep talking past each other, escalating what could've been resolved.
James brings a practical framework for identifying what actually triggers conflict (hint: it's not always what you think), and I connect the dots to the Enneagram—because knowing your type isn't just about self-awareness, it's about relational wisdom in real time.
We also wrestle with a deeper question:
How often is the conflict really about the issue… and how often is it about something underneath—process, expectations, or old emotional wounds we've carried into the room?If you've ever walked away from a conversation thinking, "That did not go how I hoped," this episode will give you a new playbook.
Because courageous conversations aren't about winning.
They're about understanding, adapting, and learning how to meet people where they are—without losing yourself in the process.And that, my friends, is a skill worth building.
Tune in next week as Anthony and I talk through a simple, practical framework for having difficult conversations.
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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" of strength. And as we talked, it became clear how many of us are still walking around with some version of that same armor—negotiating, relating, and even loving from a place of protection rather than connection.
We explored how that plays out in everyday life—how we handle conflict, how we ask for what we need, how we respond when we feel threatened or unseen. And what I appreciated most about Attia is that she doesn't just talk about tactics—she talks about transformation. About moving from control to curiosity. From winning to understanding. From guarding yourself…to actually showing up.
This is such an interesting topic that we invited Attia back for a second episode, where we go even deeper into her book Never Settle and unpack how her core negotiation strategies apply to each Enneagram type. Think of it as taking everything we talk about today and making it incredibly practical and personal for how you move through the world.
And to help you get started, Attia has put together a fantastic Negotiation by Enneagram Type cheat sheet you can grab at attiaqureshi.com/typology.
Pull up a chair. This one's going to get under the hood—in the best possible way.
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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 stay present when things get uncomfortable…when the stakes are high, the emotions are rising, and every instinct in your body is telling you to either shut down or go on the attack.
Here's the truth: every meaningful relationship—at home, at work, in leadership—requires negotiation. Not just contracts and deals, but expectations, needs, boundaries, and repair. And if you don't have emotional confidence, those conversations can go sideways fast.
That's why today's guest, Alicia Michelle, is such a gift. She brings wisdom, honesty, and a kind of steady clarity that helps us see what's really happening underneath our reactions—and how to show up differently.
Because the goal isn't to win the conversation. It's to stay in it…with courage, curiosity, and just enough self-awareness to not blow the whole thing up.
So if you've been avoiding a conversation, replaying one that didn't go well, or gearing up for one you know is coming—this episode is for you.
Let's dive in.
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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 open.
In this conversation, we explore what it means to wake up in midlife:
to grief and betrayal,
to shedding scripts you never consciously chose,
to loosening your grip on approval,
and to discovering what actually matters in the second half of life.
We also dig into how Threes navigate identity, success, and failure—especially when life refuses to follow the plan. Jen shares how therapy, embodiment work, and radical honesty helped her rebuild—not for optics, but for something sturdier and truer.
If you're in a season of change—or if life has recently pulled the rug out from under you—this episode still hits with the same quiet force. Think of it as a hand on your shoulder and a light for the next few steps.
ABOUT JEN HATMAKER
Jen Hatmaker is a bestselling author, award-winning podcaster, speaker, and fierce advocate for women living in freedom and agency. With 14 books—including four New York Times bestsellers—along with her beloved For the Love podcast, Jen Hatmaker Book Club, and more, she reaches millions with her signature mix of humor, vulnerability, and wisdom. Her newest book, AWAKE: A Memoir, (released on September 23, 2025), chronicles her raw, real-time journey through the shocking end of her 26-year marriage and surprising reinvention. She lives in a creaky old farmhouse, loves 90s country, and drinks Almond Joy creamer like it's a personality trait. Find her at JenHatmaker.com.
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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 painful work of learning how to bring those parts into the light. Along the way, we wander into territory that might feel familiar: creativity, envy, addiction, belonging, and that quiet, persistent question many of us carry: What have I done with my life?
And yet, this isn't a heavy conversation—it's a human one. There's laughter, there's tenderness, and there are a few moments where something deeper breaks through…the kind of moments that remind me why I love doing this work in the first place.
If you've ever felt like you don't quite fit—even in rooms where you clearly do…
If you've wrestled with whether your story is too much—or somehow not enough…
Or if you're trying to make peace with your past without losing who you are in the process…I think this conversation might meet you right where you are.
Come listen.
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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 using the Enneagram as a practical tool for leadership, conflict, and culture.
If you lead people, work on a team, or have ever wondered why certain workplace dynamics keep repeating themselves… this conversation might change the way you see your office forever.
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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 countertransference, explore how the Enneagram can either heal or harm in couples work, depending on whether it increases curiosity or contempt.
Whether you're a clinician or someone doing your own inner work, this episode invites you to hold the Enneagram lightly—and people reverently.
When it's used well, it doesn't replace therapy.
It deepens it.
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Download the free Therapist Discussion & Reflection Guide
Check out the Typology Institute Enneagram Assessment
Follow Ian on social at @ianmorgancron and @typologypodcast
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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, priest, and Enneagram teacher, offering guidance for using the Enneagram in a way that increases compassion rather than contempt, flexibility rather than rigidity, and insight rather than shame.
At its best, the Enneagram helps us see people not as problems to solve, but as stories shaped by fear, longing, and adaptation. Used wisely, it becomes a powerful reflective tool that deepens emotional intelligence, strengthens therapeutic relationships, and supports real transformation.
When the Enneagram is used well, it doesn't replace therapy.
It deepens it.
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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 deepest layers of pain we carry.
We explored how trauma shapes our personalities, how it imprints on the body, and why insight alone often doesn't create lasting change. As someone who cares deeply about the Enneagram and recovery, I found this especially compelling. So much of our personality structure is built around adaptation—strategies that once kept us safe but now quietly run the show.
Keith and Will explain how psychedelic-assisted therapy, when done legally and in carefully structured clinical settings, may help people access and heal places that feel otherwise unreachable. We also talk about the risks, the ethics, and the importance of discernment.
This isn't about chasing peak experiences. It's about healing what's unfinished.
If you've ever felt stuck in patterns that insight alone couldn't untangle… if you've wondered whether deeper healing is possible… this conversation might open a door.
LEARN MORE ABOUT WILL AND KEITH
WILL VAN DERVEER, MD, is a leader in the adoption of integrative psychiatry practices to treat mental health issues. He is cofounder of the Integrative Psychiatry Institute and Integrative Psychiatry Centers and cohost of The Higher Practice Podcast for Optimal Mental Health. He has published research on MDMA-assisted psychotherapy. Dr. Van Derveer has published research on MDMA-assisted psychotherapy for PTSD [1] and written book chapters in the fields of ketamine-assisted psychotherapy and other clinical applications of psychedelic compounds. His passion is finding effective relief from psychological suffering using a vast array of the most natural approaches possible. In addition to traditional medical training, He is a meditation instructor and has trained in shamanism, EMDR, somatic experiencing, internal family systems, cognitive behavioral therapy, and hypnosis.
KEITH KURLANDER, MA, LPC, is cofounder of the Integrative Psychiatry Institute and Integrative Psychiatry Centers and cohost of The Higher Practice Podcast for Optimal Mental Health. He graduated Naropa University in 2005 with a master's degree in Transpersonal Counseling Psychology, and he has practiced integrative psychotherapy and coaching with individuals, couples and groups for over 15 years. Keith's work as a coach focuses on celebrities, influencers, entrepreneurs, and CEOs who want to make huge changes in their lives, overcome long-standing patterns, and achieve greater levels of fulfillment. Keith specializes in helping individuals achieve optimal mental health and peak potential.
Social Links & Website (for promotional use)
Website - Keith Kurlander, MA, LPC
Instagram (Keith) | Instagram (Will)
LinkedIn (Keith) | LinkedIn (Will)
Psychedelic Therapy: A Revolutionary Approach to Restoring Your Mental Health and Reclaiming Your Life (Shambhala; March 31, 2026), -
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 Joe's new book, Psycho Babble, discussing how clinical terms like narcissist, OCD, and trauma have become everyday adjectives—and what it costs us when labels replace discernment, curiosity, and real relationship.
This is a grounded, honest conversation about growth, character, and what it actually means to become a healthier version of yourself—without turning self-awareness into self-avoidance.
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ABOUT JOE NUCCI
Joe Nucci is an expert in breaking down how people talk about mental health. He's a psychotherapist who corrects widely misused terms, adds valuable nuance and explains complex ideas in ways anyone can understand. He can take a mental health lens to any hot button issue. Anyone who listens to him will walk away knowing themselves and others a little better. Joe reached over 10 million people in his first 6 months of posting content. His book "Psychobabble" explores why mental health information is so confusing to navigate and how to more easily understand different perspectives about mental health. He also has an upcoming podcast, being produced by Luminary Podcasts, where he will take deeper dives into the different mental health topics that he explores on Instagram, Facebook and Tiktok @joenuccitherapy
Pscyhobabble: Viral Mental Health Myths & the Truths to Set You Free
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What happens when Enneagram Eight energy grows up, softens its edges, and learns to lead with both strength and soul?
In this episode of Typology, Ian Morgan Cron sits down with restaurateur, entrepreneur, and conscious capitalism advocate Dan Simons, co-owner of Founding Farmers, for a wide-ranging, deeply human conversation about power, protection, and what it really means to build a culture of care.
Dan is brand-new to the Enneagram—and quickly discovers he's an Eight with a strong Nine wing, a compelling combination that blends moral clarity with empathy, decisiveness with nuance, and fire with calm. Together, Ian and Dan explore how Eights aren't just challengers—they're often defenders: leaders shaped by early experiences of injustice who instinctively stand up for the vulnerable.
Along the way, they talk candidly about:
Why anger can be a tool rather than a liability when it's consciously harnessed
How leadership failures are often listening failures (and the three most powerful words a leader can say)
How putting emotional well-being on equal footing with profit actually increases performance, retention, and long-term value
What a healthy workplace should feel like when you walk through the door (hint: think Labrador retriever, not shark tank)
This is a masterclass in evolved leadership and a hopeful vision of capitalism done with conscience. If you're a leader, an Enneagram Eight, or someone longing for work cultures that don't crush the human spirit, this conversation will leave you both challenged and encouraged—in the best possible way.
Listen in and pull up a chair. There's a seat for you at this table.
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About Dan Simons
Dan Simons is regarded as a leading voice in mission-driven business practices, known for championing people-centric culture and responsible industry standards while developing systems that deliver profitability. He and his partner, Michael Vucurevich, are Co-Owners of Founding Farmers Restaurant Group in partnership with the North Dakota Farmers Union. Their goal is to generate profits for American family farmers, earn farmers a larger share of the food dollar, and influence the sourcing decisions of suppliers and others in the hospitality industry. They operate eight sustainably run restaurants, one DC-based distillery, and a full service catering and event design company. He teaches courses at The George Washington University, hosts a podcast (Founding DC), and sits on the advisory boards of the DC chapter of Conscious Capitalism, OpenTable, and the Health Action Alliance Women's Health at Work Program. He blogs at www.DanSimonsSays.com and can be found across most social channels @DanSimonsSays. Visit https://www.dansimonssays.com/ to learn more.
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What happens when the worst thing you've been afraid of actually happens—and you're still standing?
In this episode of Typology, I sit down with songwriter Brad Warren—an Enneagram Six, a man in long-term recovery, a husband, a father, and someone who has walked straight through unimaginable grief and come out the other side with humility, humor, and hard-won wisdom. Brad is the kind of person who tells the truth without posturing, who can laugh at himself without diminishing himself, and who understands—deeply—that fear doesn't disappear just because you name it. But naming it does change the game.
We talk about the Enneagram Six's instinct to scan the horizon for danger, to rehearse conversations that never happen, and to catastrophize not because they're weak—but because they care. A lot. Brad shares how losing a child forced him to face his worst fears head-on, and how recovery, faith, and accountability helped him learn the difference between imagined catastrophe and lived reality. There's a kind of quiet courage in the way he describes trusting God—not a God who's looking to smite him, but one who's patiently inviting him to rest.
Along the way, we explore humor as both a survival strategy and a spiritual practice, the surprising connection between humility and laughter, and how Sixes learn to move from fear-driven vigilance to faith-filled presence. We also touch on marriage, loyalty, religious deconstruction with gratitude instead of bitterness, and the life-saving power of people who are willing to tell you the truth when your mind is lying to you.
This episode is funny, tender, honest, and deeply human. It's about fear—but it's even more about trust. And what it looks like, day by day, to choose it anyway.
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About Brad Warren
Brad Warren is a Nashville-based songwriter and artist best known as one half of the hitmaking Warren Brothers. He has co-written major country hits recorded by Tim McGraw, Toby Keith , Keith Urban, Faith Hill , Martina McBride, Dierks Bentley, Jason Aldean and more.
Brad is also the host of the Good Grief Good God podcast. He and his wife Michelle lost their oldest son Sage in 2020 and the podcast is in honor of him. Brad covers an array of other topics (recovery, God, mental and physical health, and The Music Business) as well as grief. Guests have ranged from Sheryl Crow and Amy Grant to Scott Hamilton and Charles Esten.
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