Not All Who "Wonder" Are Lost
The Courage to Be Curious – Risk, Play, and Discover
In September 2022, my wife and I took a little 82-mile walk.
It sounds more poetic than practical, especially when you consider the months of planning, training, and questioning that led up to it. But that’s how most real adventures begin — not with a map, but with a challenge.
In this case, the challenge came quietly from the pages of Arthur Brooks' From Strength to Strength:
“Go for a walk.”
I’d been thinking a lot about what life might look like in my sixth decade. I committed to getting serious about my values, purpose, and how I wanted to spend the rest of my life, professionally and personally.
Brooks’ book resonated with something in me. But as usual, I was more comfortable thinking about it than doing something.
That’s where my wife comes in. She’s the planner, the realist, and the one who knows how to turn ideas into action.
While I was busy underlining passages and philosophizing about my next phase, she was booking flights to Italy.
She challenged me to move from curiosity to courage in the best possible way. And so we began what’s now affectionately known in our home as simply The Walk.
The Path of the Gods
The Via degli Dei — or Path of the Gods — is an 82-mile trek from Bologna to Florence across the Tuscan-Emilian Apennines.
It’s not a pilgrimage or a race. There’s no prize for finishing.
But every step brought us something worth discovering about the country, the Italian people, each other, and ourselves.
I didn’t know what I was looking for when we started. I just knew that something in me needed to get unstuck. And walking, as it turns out, is a profoundly underestimated way to begin.
We faced physical doubts (can we actually do this?), emotional resistance (why am I doing this again?), and mental friction (how did I let myself get talked into this?).
But with each step, those questions slowly transformed. Fear turned into focus. Resistance into rhythm. And eventually, thinking gave way to being present.
Curiosity Isn’t Passive
That’s the thing about curiosity — it often starts quietly. A nudge. A sentence. A wondering. But it doesn’t mean much until it leads to movement.
Reading a book can stir emotion, but transformation happens when you put the book down and take the first step into the adventure.
It’s one thing to ask, “What would it be like to do something different?”
It’s another to buy the plane ticket. Strap on the backpack. Start climbing the hill.
Most of us like the idea of exploration — but not the discomfort. We say we’re curious, but often we’re just cautious.
We want discovery without disruption.
We want growth without giving anything up.
But growth requires risk. And often, play.
The Risk of Play
We treated this walk like an experiment, with minimal expectations and a commitment to figuring it out as we went. That’s what made it feel like play in the truest sense: low-stakes, high-reward exploration.
We carried only what we needed, made decisions on the fly, and allowed ourselves to be a little lost. (Sometimes more than a little.)
The journey wasn’t glamorous. There were blisters. Bad weather. Wrong turns. And yet, that’s where the richness was.
There was no “next thing” to chase, no itinerary to maintain. Just the next step. And the one after that. This wasn’t about achieving — it was about experiencing.
What Stops Us
There are a hundred reasons we don’t explore:
- I’m not in shape.
- I’m too busy.
- I’ll fail.
- I don’t know how.
- What if it’s hard?
All of those thoughts crossed my mind before we set out.
And yet, the walk taught me that you don’t need to be perfectly prepared. You need to be willing. You need to show up. And be open.
Curiosity doesn’t demand expertise. It demands courage.
It asks: Are you willing to wander and wonder?
A Simple Achievement
There was nothing spectacular about finishing the Via degli Dei. No medals, no cheering crowds. Just two people arriving in Florence with tired feet and stronger hearts.
And yet, it felt like one of the most meaningful things I’ve ever done.
Reflect a Minute
What are you curious about, but afraid to explore?
What’s one low-stakes experiment you could try this week, not for the outcome but for the experience?
Want to journal but not sure how to get started? How about a gentle nudge in the right direction?
Try the HHN Journaling Coach—a companion designed to help you reflect, reset, and reconnect with yourself through thoughtful prompts and questions.
Deep thinking meets life’s detours—one prompt at a time.
