25. The Power of Doing Hard Things: How Facing Fear, Letting Go & Reinventing Yourself Unlocks True Freedom

Limitless: Unlocking Your True Potential

“I told my daughter, ‘Logan, there’s a real risk you could die on this trip.’ And she said, ‘Mom, I’d rather die under a palm tree with my family than in this hospital every day. I want to live my life.’”

When Jenn Montgomery-Lay’s daughter was diagnosed with cancer for the fourth time and undergoing treatment, life as she knew it shattered. Faced with the unimaginable, Jenn and her family made a radical choice that defied expectations and fear. They took Logan out of hospice care and embarked on a year-long journey around the world, reclaiming life on their own terms.

But this was just one of many turning points in Jenn’s evolution. She had to navigate the deep identity shifts of breaking cycles, releasing control, and stepping into her midlife "level-up era." Letting go of perfectionism, learning to embrace uncertainty, and prioritizing her own growth became essential steps in unlocking her freedom. In this deeply moving conversation, Jenn shares how she found strength through discomfort, courage in reinvention, and healing through connection.

Today on Limitless:

- Breaking Free from Old Identities – From high-achiever to full-time caregiver to world traveler and entrepreneur

- Reclaiming Life Through Radical Choice – Taking Logan out of hospice and choosing adventure over fear

- The Transformative Power of Travel – How stepping outside of routine redefined what "living" really meant

- Letting Go of Control and Embracing the Unknown – Moving from survival mode to intentional exploration

- Setting Boundaries and Embracing Authenticity – Releasing people-pleasing and external validation

- Navigating Fear and Uncertainty – Learning to coexist with fear instead of letting it dictate choices

- Healing Through Connection and Community – The profound relationships that shaped Jenn’s journey

- The Midlife "Level-Up Era" – Reinventing herself and stepping into purpose-driven entrepreneurship

If you have ever felt stuck in fear, trapped by expectations, or uncertain about your next chapter, Jenn’s story is a powerful reminder that you can redefine your life by making bold, courageous choices one step at a time.

Connect with Jenn:

Follow Jenn’s journey and insights on her blog: Life All Over the Map

Connect with Jenn on Instagram: @lifealloverthemap

Connect with Fiona:

Private Coaching: Work with me

Instagram: @fionawalshcoaching

LinkedIn: Fiona Walsh

Email: [e-mail]