EP 175: Why Freedom Needs Structure: How Jackie Dragone Builds Success on Her Terms

Welcome to a brand new episode of the You Can Call Me “Bossy" podcast. Today, I got together with Jackie Dragone, a powerhouse coach and fierce advocate for women embracing their true selves—no matter how “bossy” or “too much” they might be perceived. Jackie shares her journey from fitness coaching to becoming a leading business and messaging coach for women, highlighting the importance of coming home to your own voice and message, especially in an online world obsessed with performance and comparison.

Together, Jackie and I dig deep into topics like human design, letting go of control, and the myth that freedom comes without structure. Jackie opens up about the pivotal moments that have shaped her path—like moving to Mexico and redefining her business not for the paycheck, but for true alignment and fulfillment. If you’ve ever felt held back by fear of judgment, people-pleasing, or uncertainty, this episode is packed with real talk and practical wisdom to help you break free and step forward, messy and all.

Key Takeaways:

• Reflection on the importance of being rooted in a long-term vision.
• Emphasizes on self-study and choosing methods that work personally over external “shoulds.”
• Encouraging self-examination of who your decisions really are for—yourself or others.

Key Timestamps

[6:33] – Embracing Uncertainty and Trust

[11:27] – Natural Explorer Mindset

[16:22] – Authenticity Leads to Success

[19:26] –  Self-Discovery for Empowered Women

[25:05] –  Ignite Your Voice

Episode Quote

•   "But what if you become somebody different? What if you go back intoyour own heart, your soul, your desire, what you really believe that you were created to do on this earth? Like, won't the money just follow that?" - Jackie Dragone

Episode Resources

• Instagram: @Iamjackiedragone
• CLICK HERE to book a discovery call for LevelUp

If you enjoyed this episode and are excited for more, please be sure to SUBSCRIBE and write a review to help build momentum and support the show (5-stars would be AWESOME!)
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