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.

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.

"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.

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.

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.

Susan 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.

If this episode resonates, follow the show so you don't miss future conversations on the Enneagram, relationships, and spiritual growth.

Know 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.

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.

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.

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.