This morning, 7:13 AM, Croatian hat settled on my head, backpack loaded with gear I probably don’t need. The familiar circuit calls—out the front door, down to the path, into the rhythm that unwinds whatever the mind has been tangling.

The weekend just passed brought a new soul into our family circle. A tiny human, barely breathing outside the womb, is already reshaping the geometry of time around her. My son and his partner, young and bright-eyed in that particular way of first-time parents, hold this small mystery while I watch from the strange vantage point of a newly minted grandparent.

From here, I can see it all clearly: the great arc of time stretched before me like a walking path. On one end, my son’s young family at the beginning of their story, all possibility and sleepless wonder. On the other end, the great-grandparents in their seventies and eighties are sliding into the twilight of their years. And here I stand in the middle, the trajectory of my life made visible through them.

It’s this unique position, actually, when you think about it. You’re seeing what your past looked like—young family, all that energy and chaos. And you’re seeing what your future looks like, too, in 20 years or so.

The circle of life isn’t just a Disney lyric anymore; it’s the living geometry of generations, each one watching the others from their place on the arc. If I look at this through the lens of a classic story, I see myself entering the beginning of Act III.

The Questions That Matter

This middle space brings different questions than the earlier acts. Not “What do I want to become?” but “What legacy am I leaving?” Not “How do I succeed?” But “What stories will they tell about Pops when I’m gone?”

When I held my son for the first time, I was nearly the same age he is now. Our parents then were the age we are today. It’s this beautiful symmetry—time folding back on itself like the path I’m walking this morning, each generation experiencing the same wonder, the same protective fear, and the same overwhelming love for something so small and vulnerable.

But what changes in this middle position is perspective. When you’re young with a baby, you’re just surviving—feeding, changing, soothing, hoping you don’t break this precious thing. When you’re watching your child become a parent, you’re witnessing the miracle from a different angle entirely. You see the continuity, the great river of life flowing from one generation to the next.

The Grandfather’s Craft

So what does it mean to be a grandfather in this story? Not just biologically, but as a role, a craft to be learned?

I think about my own grandfather—the stories that have survived about him, the fragments of wisdom that somehow made it through the decades to shape who I am today. Most of what he said is lost to time, but the essence of him, the way he moved through the world, somehow got passed down from my father to me.

Now I’m the one creating those fragments for this tiny girl sleeping in Ludlow. What essence will I leave behind? What will she remember about Pops when she’s older?

The weight of this hits me about halfway through my wisdom walk, near the old tree that marks the return point. I’m not just responsible for my own story anymore. I’m helping to author the opening chapters of hers, laying down the foundation stories she’ll carry forward.

The Wisdom Walk Philosophy

This is where the barefoot philosopher thing starts to make sense. Not as some marketing gimmick or personal brand, but as a way of being that’s worth passing down. The grandfather who goes for wisdom walks, who thinks out loud, who wonders about the big questions while his feet find familiar paths.

Maybe that’s what philosophers are really for—not to write dense academic papers that gather dust, but to model a way of engaging with life that’s curious, contemplative, and present. To show the next generation that it’s okay to take time to think, to walk, and to wonder.

I imagine taking her on these walks when she’s older. Little legs trying to keep up, asking those beautiful questions that only children ask: “Why do leaves fall down?” “Where do thoughts come from?” “What makes the sky blue?” And instead of rushing to Google for answers, we’ll walk and wonder together.

The Story I Want to Tell

The morning mist is lifting now, and I can see the Holy Well ahead—that ancient spring where people have been coming for centuries seeking healing, wisdom, and connection to something larger than themselves. It occurs to me that this is exactly what I’m doing on these walks, what I want to teach her to do: to seek out the sacred in the ordinary, to find wisdom in movement, and to trust that the answers we need often come when we stop trying so hard to find them.

When she asks about her grandfather someday, I want the stories to be simple but true: He went for walks. He thought about big questions. He paid attention to small things. He believed that wisdom came from living fully, not from accumulating facts.

I want her to know that he chose presence over productivity, curiosity over certainty, wonder over worry. That he tried to live authentically, even when—especially when—the culture around him was obsessed with performance and appearances.

The Raw Experience of Love

Here’s what I’m learning as I circle back toward home: the most profound experiences can’t be manufactured or marketed. You can’t optimise your way into the feeling of holding your grandchild for the first time. You can’t productivity-hack the moment when she first recognises your face and smiles.

This is raw experience at its most essential—love that requires no craft, no strategy, and no improvement. Just presence. Just showing up fully to the miracle of another human being who carries your family’s story forward into an unknown future.

All my life I’ve been trying to learn crafts—writing craft, video craft, and marketing craft. But maybe the most important craft I need to master now is the craft of being a grandfather. And that craft is surprisingly simple: Pay attention. Show up. Love without condition. Walk and wonder and trust that the wisdom will come.

Coming Home

The familiar gate appears ahead, my circuit complete. Backpack heavier now with the weight of these thoughts, but my step lighter somehow. The questions that seemed so urgent an hour ago—about careers and content and finding my authentic voice—feel less pressing now.

I’m a grandfather. That’s the story that matters. Everything else is just details.

The little one sleeping in Ludlow will wake soon to a world full of wonder and confusion, beauty and pain. My job isn’t to prepare her for it all—that’s impossible. My job is to show her that it’s possible to walk through it with curiosity, with presence, and with love.

To show her that wisdom isn’t something you arrive at but something you practise daily on whatever path you choose to walk.

The Holy Well bubbles quietly behind me as I head toward home, carrying this ancient blessing forward: may you find healing in movement, wisdom in wondering, and love in the simple act of paying attention.

Time to see what we can make of this beautiful, ordinary morning.

Pops and Rosie sharing a barefoot philosopher’s moment.