Typology

Courageous Conversations: The Inner Work that Builds Confidence


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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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TypologyBy Ian Morgan Cron

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