Midlife as Pilgrimage

A New Series for the Written Word

Hey friend,

If you’ve listened to my new podcast, A Wayfinder’s Guide to Life (episode 5 is out now on Apple & Spotify), you know I’m fascinated by the space we find ourselves in at midlife: that raw, sacred in-between where the life we built starts to feel too small, and something quieter, older, begins to call.

I’ve shared a lot of these reflections through the podcast. But for those who are drawn more to ink than audio, I want to offer something here: a written companion to that unfolding journey.

Over the next while, I’ll share a series of reflections on midlife through the lens of the Hero’s Journey (or Heroine’s Journey).

Yes, the same structure you’ll find in countless myths, movies and sacred stories.

But this isn't about dragons or distant lands. It's about your life. That moment when the old map no longer fits. The grief that rises. The resistance. The quiet voice of truth. And, if we follow it… the return to something more essential and alive.

These essays won't be podcast summaries. They’re here for those who prefer a slower rhythm. For those who underline, reread, and find themselves pausing mid-sentence because something stirred inside you. They’re for those who want not just insight, but resonance.

NOTE: Although my primary audience for writing and the podcast is entrepreneurs, if you’re not of an entrepreneurial persuasion, you’ll still find lots of value in this series.

Why This? Why Now?

I’ve spent the last decade walking alongside entrepreneurs and leaders in the thick of midlife. People who’ve done all the right things and still feel that ache for something more. That ache isn’t a failure. It’s a signal. A compass, if we’re brave enough to listen.

The Hero’s Journey is a useful and valuable way to frame what your soul already knows. To make meaning of your confusion and suffering. If you follow along, I think you’ll agree.

The transformation doesn’t come from more achievement, more speed, or more strategy. It comes from stepping away from the noise and into wild places. The ones where we are asked to let go, to listen, to become something new.

If you’re in that place, or even approaching it, I hope this series offers something meaningful. Not answers, necessarily. But language. Permission. A sense that you’re not alone.

What to Expect

Each post will explore a stage in the soul’s journey:

• The Call: the inner whisper you’ve been trying to ignore

• The Resistance: the strategies we use to stay safe

• The Threshold: when we say yes and leap into the unknown

• The Descent: when everything starts to unravel

• The Guides: those unexpected people that help us see

• The Trial: facing what we’d rather avoid

• The Revelation: beauty that breaks us open

• The Return: bringing soul back into our daily lives

• The Way: what comes after success

• The Invitation: becoming a guide for others

I’ll weave in stories from my own life and the Wayfinders community. I’ll offer soul prompts and small practices you can carry with you. And I’ll try to meet you where you are, not where you’re supposed to be.

(NOTE: The written series follows the same stages of the Hero’s Journey I’m exploring in the podcast, but 5 weeks behind. Let’s just say launching a podcast is a LOT of work, and it took up any available bandwidth I might have had for writing).

If this speaks to you, I’d love for you to follow along (or subscribe if you’re encountering my writing for this first time).

The old map may be fading. But something deeper is beginning to emerge: a path shaped not by expectation, but by essence.

We’ll walk it together.

With heart,

Mike

---

P.S. – Ways to Continue the Journey

If you’re looking to keep walking the path with me, here are a few ways to do so:

Join My Mailing List: Sign up at https://way-finders.com/events-list to get notified when I host new events for soulfully-minded entrepreneurs.

My Podcast: A Wayfinder’s Guide to Life Stories, conversations, and soul-maps for the journey inward. Season One’s ten episodes look at midlife through the lens of the hero’s journey. Follow the show on Spotify or Apple.

Monthly Soul Talks: Intimate, live community calls where we drop the masks, speak the truth, and hold space for the questions that really matter. **Upcoming events will be posted at https://lu.ma/soultalks (**subscribe to the calendar to get notified)

Upcoming Adventures: Want to journey with us into the sacred wild? Check out upcoming Wayfinders Adventures in Mongolia, Arabia, Bhutan and more.

For Entrepreneur Dads in Toronto: Join Around the Fire, an invitation-only space for Toronto-area entrepreneur dads to connect in depth and truth. Subscribe here to be notified about future gatherings.