The Itch You Shouldn’t Ignore—with Kaitlin Files-#149 episode artwork

EPISODE · Apr 30, 2026 · 30 MIN

The Itch You Shouldn’t Ignore—with Kaitlin Files-#149

from Dare On with Jodi · host Jodi Silverman

You know that itch—the one deep inside that tells you something’s off or that there’s something more waiting for you? That’s not restlessness—it’s your intuition.In this episode, Jodi sits down with attorney and entrepreneur Kaitlin Files, who shares how she turned an unexpected career detour into her most daring move yet: launching her own law firm during the pandemic.Together, they explore:How to tell the difference between fear and intuitionWhy daring moments often begin with one simple question: Why not me?The power of believing in yourself before the world doesAnd what it really takes to push through doubt and start againIf you’ve been feeling that itch for something new, this conversation will inspire you to stop ignoring it—and start daring on.👉 RESET YOUR SELF TALK with Jodi's 7 Day Mini Reset HEREMentioned in this Episode:Kaitlin’s law firm: Workers’ Compensation & Injury LawDIY with Beth Allen (connection that brought them together)“Scream Your Dream” by Cheldin RumerDare of the Week: Dare to meditate. Whether it’s your first time or your hundredth, pause long enough to listen to the whisper inside.Send me a quick note/message- what stood out in this episode! 🎙️ You've been listening to me—now I want to meet YOU.  Join me on Substack, where Dare On goes beyond the podcast. We're having real conversations about midlife, what's next, the things we're struggling with, and the lives we still want to create. You'll find live gatherings, connection, encouragement. Subscribe for FREE and come introduce yourself HEREI can't wait to meet Subscribe to my Substack HEREStep into the Dare On Circle HERE

Episode metadata supplied by the publisher feed · Published Apr 30, 2026

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You know that itch—the one deep inside that tells you something’s off or that there’s something more waiting for you? That’s not restlessness—it’s your intuition. In this episode, Jodi sits down with attorney and entrepreneur Kaitlin Files, who shares how she turned an unexpected career detour into her most daring move yet: launching her own law firm during the pandemic. Together, they explore: How to tell the difference between fear and intuitionWhy daring moments often begin with one simple...

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The Itch You Shouldn’t Ignore—with Kaitlin Files-#149

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