Courageous Conversations: The Inner Work that Builds Confidence

Typology

Ian Morgan Cron

Christianity, Health & Fitness, Religion & Spirituality

4.7 • 3.2K Ratings

🗓️ 2 April 2026

⏱️ 60 minutes

🔗️ Recording | iTunes | RSS

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Summary

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.

Transcript

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0:00.0	Hey folks and welcome to Typology, the show on which we explore the mystery of the human personality and the mystery of the great human adventure all through the lens of the Enneagram.
0:13.4	My name is Anthony Skinner, your producer and co-host. This week, we're kicking off a multiple week series tackling something that quietly shapes almost every outcome in your life.
0:23.6	How you handle what's inside of you when something outside of you really matters.
0:29.6	Because before you ever step into a hard conversation, before you advocate for yourself, before you negotiate anything,
0:36.7	you're negotiating with your own
0:38.4	internal world, your thoughts, your emotions, your reactions. Because if you can't regulate
0:44.1	what's happening inside of you, it's really hard to show up well in any conversation that
0:48.9	matters. Over the next few weeks, we're digging into the foundations of emotional confidence,
0:54.8	strategies for negotiating, and how to have difficult conversations. As you listen to this series
1:01.8	over the next few episodes, we invite you to pay attention to the conversations that come to
1:06.8	mind, the ones you have been putting off, the ones you've been replaying in your head, or the
1:12.1	ones you know that are coming up. Because our hope is that by the end of this series, you won't
1:18.4	just understand yourself better, you'll actually feel more equipped to step into those moments
1:22.9	with clarity, courage, and a whole lot more skill. All right, so let's start at the root with a fresh
1:29.4	look at our conversation with Alicia Michelle and her ADD method of emotional confidence to learn
1:36.7	how to slow down your inner world so you can show up with intention in your outer one. Hey, that's it for
1:43.3	me, Anthony Skinner. So excited you're here.
1:46.5	Without any further ado, let's get to the man of the hour, Ian Kron.
1:59.5	Well, typology friends, welcome back.
2:02.3	And today, man, we got a rich conversation with my friend, Alicia Michelle.
2:08.4	Anya Graham 1.
2:09.9	You heard all the wonderful things that she's been doing at the top end of the show.
	...

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