Remember when you last listened to your soul?
Call it your heart, your gut, or your intuition if that feels less esoteric.
Remember that feeling in the pit of your stomach, when you quit that job that did a great job of paying your bills but a terrible job of feeding your soul?
Or when you left a relationship that was no longer working to step into the great unknown of singlehood and loneliness, in service of your heart?
That is the threshold.
The threshold is the moment when something in you says yes… the yes that surfaces when staying the same begins to cost more than stepping into the unknown.
There’s a sacredness to this moment. You may still feel unsure. You may not have words for it yet. You’re a little bit terrified.
But the shift has already happened. The old way has lost its grip, and something deeper is pulling you forward.
In this mini-series, we’re exploring midlife through the lens of the Hero’s Journey, echoing in the written word what I’ve been exploring via Season One of my podcast, A Wayfinder’s Guide to Life (follow on Apple or Spotify)
The first post was about The Call, that ache that arrives when the life you’ve built no longer matches the person you’re becoming.
The second focused on The Resistance, the clever ways we talk ourselves out of listening and staying stuck.
Together, these stages prepare us for this moment. The edge. The crossing. The threshold.
The In-Between
Sometimes we’re pulled across the threshold. A layoff. A diagnosis. The end of a marriage. Other times, we choose it willingly: a quiet moment of clarity, a feeling in the body that says, enough.
Either way, once you’re here, the old map no longer applies. You are no longer who you were, and not yet who you are becoming. This space can feel uncertain and raw. You may want to go back, but something in you knows you can’t.
This is the terrain where we begin to follow different instructions. Not from logic or social norms, but from the wisdom that lives beneath all that.
The threshold invites you to move from instinct, not strategy.
Small Steps Matter
There’s a myth that real change has to be dramatic. The big move. The grand exit. The new identity.
But the truth is, thresholds are often crossed in far humbler ways.
It might be as small as saying no to a project that doesn’t feel aligned. Telling a friend you’re not okay. Going for a walk without your phone. Trying something you’ve always been curious about, even if it makes you feel awkward.
The threshold asks for one thing: a single step. Not because you know where it leads, but because you know you can’t stay where you are.
Follow Aliveness
One of the core principles we hold on Wayfinders Adventures is to have fun and be a little ridiculous. This isn’t fluff. It’s medicine.
Play gives the soul room to breathe. It cuts through the heaviness and invites something essential to the surface. When we loosen our grip on how things are supposed to look, we often find ourselves more connected to what is true.
So if you’re feeling stuck or heavy, try something delightfully strange. Sing loudly in the car. Join a dance class you feel wildly unqualified for. Learn to bake bread with your eyes closed.
Let joy lead, even if just for a moment. Let aliveness be your compass.
A Threshold of My Own
In 2018, I found myself facing a threshold I could no longer avoid. I had spent over two decades building a company from the ground up. From the outside, it looked like success. Inside, I was unraveling.
I tried to ignore the signs. I told myself I’d feel better once we hit the next milestone. But I was numb. And tired. And done.
Two things cracked something open in me.
The first was reading Ego is the Enemy by Ryan Holiday.
I saw myself in every chapter. So many of my ambitions had been driven by the part of me that still needed to prove I mattered.
The second was a single question asked by my friend Philip McKernan: “Where in your life are you seeking validation, and why?”
That question hit hard. I saw my big, bold goals for what they were. Not expressions of truth, but bids for approval. I imagined achieving them and felt nothing but emptiness.
That morning, I let it all go. I walked away from a company I had spent over 20 years building. I didn’t have a new blueprint or a five-year plan. I just knew I couldn’t keep going the way I had.
That was my threshold. And it changed everything.
NOTE: I am thrilled to say that I’m now, eight years later, collaborating with Philip McKernan on an incredible event in Iceland in May of 2026 called Unshakeable.
Over the course of this six-day retreat at a spectacular private resort north of Reykjavik, we’ll explore the twin themes of resilience and adaptability through coaching, group exercises, reflection, and adventures in this wild landscape.
You’ll leave with clarity, tools and practices that will prepare you for the coming era of rapid change, as well as a peer group of fellow entrepreneurs to support you on your journey. As of July 17, the event is over 60% sold, so get your application in today!
The Soul Moves Differently
We’re taught to wait for permission. For clarity. For guarantees. But the soul doesn’t operate on those terms. It speaks in longings, in nudges, in quiet invitations.
It will not shout. But it will wait.
You don’t need to see the whole path. You only need to take one honest step.
This week, try one small, soulful experiment. Something playful. Something a little strange. Something that stirs even the smallest sense of aliveness.
Then notice what it awakens in you.
Three prompts to explore this week:
What must you leave behind to move forward?
Where are you currently seeking validation, and why?
What does your next threshold moment ask of you, and are you willing to cross it before you feel ready?
May your next step be a true one.
