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June 10, 2025 19 mins

There comes a moment when staying put becomes more painful than stepping into the unknown. In this episode of The Wayfinder’s Guide to Life, Mike explores that sacred moment of decision, when the soul whispers “it’s time” and you find yourself on the edge of the map.

We talk about what it means to cross the threshold in midlife: to choose courage over comfort, to honour the quiet ache for something more, even when the path ahead is uncertain. 

Mike shares the personal story of walking away from the company he built over two decades, and how a friend’s powerful question cracked open a new direction... one rooted in joy, curiosity, and the wisdom of small, soulful experiments.

This is not about grand gestures or burning it all down. It’s about listening. Following breadcrumbs. Trusting the pull of what makes you feel alive. 

Whether you’re on the edge of your own threshold or just beginning to sense it approaching, this episode offers a gentle invitation. Not to leap, but to take one small step into the unknown.

EXERCISE:
This week, try a small, soulful experiment. Follow one breadcrumb. Something playful, curious, or quietly bold. Let joy, not logic, be your compass. It doesn’t have to make sense. It just has to stir something in you.

PROMPTS:

  1. What must you leave behind to move forward?
  2. Where are you currently seeking validation? And why?
  3. What does your next threshold moment ask of you, and are you willing to cross it before you feel fully ready?

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CONTINUE THE JOURNEY:

✴️ Join a Wayfinders Adventureway-finders.com/adventures

Wayfinders Adventures are soul-stirring retreats for entrepreneurs and leaders ready to reconnect with their deeper selves and others walking the same path.

✴️ Join Mike & Philip McKernan in Iceland in May 2026 www.unshakeable2026.com

Unshakable: Iceland is a 5-day retreat at a private, secluded Icelandic sanctuary, led by me and Philip McKernan. For entrepreneurs who know the world is changing, and want to meet it with stillness, strength, and truth.

✴️ Join a live Soultalks callhttps://lu.ma/soultalks

Each month, we gather for a soulful online conversation: a space to slow down, reflect, and connect with others navigating the same questions.

✴️ Get notified about upcoming entrepreneur events: https://way-finders.com/events-list

Get a weekly email with a curated selection of events around the world for growth-minded entrepreneurs.

✴️ Subscribe to my Substackwayfinders.substack.com

For reflections, stories, and soul prompts between episodes, join me on Substa...

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