104: From Playing It Safe to Living Fully: How Jennie Milton Turned Fear Into Freedom

In this inspiring episode of Flying Upstream, host Kristyn Medeiros sits down with adventurer and women’s empowerment advocate Jennie Milton to explore how living with courage can completely transform your life. Jennie shares her journey from conventional living to bold adventure, beginning with a life-changing trip to Alaska that sparked a radical pivot.

Through powerful storytelling, Jennie unpacks the role of fear tolerance in personal growth, how adventure and self-discovery go hand-in-hand, and why she believes courage is a teachable skill. From leading kite camps that empower women to writing children’s books on bravery, Jennie's story is packed with insights on overcoming adversity and embracing an authentic, alternative lifestyle rooted in passion and purpose.

Keep up with Jennie on her website and socials such as Instagram, YouTube, and Facebook.

Chapters:

00:00 — The Call to Something More
02:15 — Jenny’s Journey: From Ordinary to Intentional
11:32 — Facing Fear and Finding Freedom
21:23 — The Science and Soul of Fear Tolerance
28:39 — Empowering Women Through Adventure
37:43 — Turning Pain Into Purpose: Books That Inspire
48:19 — A Letter to Her Past Self

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