EP 261 The Truth About Confidence: Why Some Retreat Leaders Struggle to Fill Their Events with Nathan Jamail

Confidence isn't just mindset crap. It affects your pricing, your messaging, your sales conversations and your boundaries. And ultimately - whether your retreat fills or flops. In this episode, Shannon is joined by leadership expert, sales strategist, and bestselling author Nathan Jamail (she is biased, but he is pretty damn amazing) to unpack the real reason many retreat leaders struggle to sell out their events: lack of business confidence. They discuss: Imposter syndrome in the retreat industry Underpricing rooted in insecurity Overexplaining instead of leading What confident messaging actually sounds like How to build real, earned business confidence They also share that this episode was recorded in their new studio space in Austin - and you can now watch the full conversation on YouTube. If you've ever doubted yourself while launching a retreat, this episode will challenge and strengthen you. What You'll Learn Why confidence directly impacts conversions The hidden cost of underpricing How retreat leaders accidentally repel buyers The difference between loud marketing and confident leadership The discipline required to build real business confidence Key Takeaways Imposter syndrome doesn't disappear - it's managed through action. Underpricing signals insecurity to your audience. Overexplaining weakens authority. Confident leaders make clear decisions and stand by them. Confidence is built through preparation, skill, and repetition - not affirmations alone. Watch on YouTube This episode was recorded in our new studio space in Austin - go watch the full conversation on YouTube. Learn more about Nathan Jamail: Join Nathan and Shannon at the Forum:

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EP 261 The Truth About Confidence: Why Some Retreat Leaders Struggle to Fill Their Events with Nathan Jamail is an episode from Happy Hour Podcast with Dee and Shannon by Shannon Jamail.

This episode is 25:44 long.

This episode was published on Mar 12, 2026.

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