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.

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.

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.

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.

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.

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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