In Episode 121, Jeff Krommendyk, insurance expert with One Digital Insurance Agency and co-host of the Expert Network Team, recounts the eight-day, 85-mile Tuscan stretch of the ancient Via Francigena he and his wife Leslie recently hiked with a small discipleship cohort—a journey that blended rigorous daily walking with deep prayer, marriage-focused vision-casting, and community. The pilgrimage became a transformative marriage retreat, giving the couple clarity about merging their complementary callings—his executive and spiritual coaching passions with her talent for curating immersive experiences—into future retreats that nourish body, soul, and spirit. Jeff describes how time in nature, shared spiritual practices, and new friendships left them energized, unified, and inspired to design meaningful, adventure-infused growth experiences for others in the next season of life.
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Leslie and I just got back from an eight-day pilgrimage. We hiked 85 miles of the Via Francigena, which is an ancient spiritual pathway that runs from Canterbury, England down through France, into northern Italy, and ultimately to Rome. We did the Tuscany section of that trail.
It was a marriage retreat slash vision-casting event. The timing was perfect. It was part of a discipleship cohort I joined earlier this year, in February. There were six other couples on the trip.
We spent intentional time walking—12 to 18 miles a day—and planning, dreaming, and praying. Just a lot of time with the Lord. It was truly a life-changing event for us.
I think it brought Leslie and me closer together as a couple. For most of our married life, we’ve raised kids and had our own faith journeys. We’ve moved in the same direction but hadn’t fully merged those journeys. I was building our business; she was raising our children.
Now, we have a shared vision for what the next season of life might look like. It’s vocational too—her passion for creating immersive experiences, and mine for coaching, executive leadership, and spiritual guidance. We’re beginning to imagine retreats that combine these elements—retreats that nourish body, soul, and spirit.
Maybe they’ll be held in the mountains of Colorado, up in Winter Park, or in Europe, like the trip we just took. Leslie handles logistics and lodging. We add some physical activity, some deep content, and a lot of intentional space. For the first time, we’re dreaming together about what’s next.
And thankfully, we’re not under pressure to monetize this dream right away. That gives us the freedom to explore it and see where God takes us.
I don’t have all the answers yet. When I walk out of the office for the last time, I plan to take a sabbatical—maybe 3, 6, or even 12 months—to decompress, celebrate, and reboot. Then I’ll come back to the second half of life with a clean slate, a blank canvas.
Karl and the team here will make sure we’ve got food on the table until then!
I’m not a visionary or a serial entrepreneur like some of our friends. But I could see myself getting involved in a new venture—maybe someone else has the vision and I help bring it to life. I’m more of a maintainer than a starter, but I love helping things grow.
What excites me most is that Leslie and I are on the same page. We have a shared vision. And this trip—this pilgrimage—wasn’t just a vacation. It was something more. It fed our bodies, our souls, and our spirits.
We did it with six other couples from around the country—people we didn’t know before and who are now lifelong friends.
The physical activity, the natural beauty, the spiritual practices—all of it filled us up. We came home energized and full of purpose.
I’m now a huge advocate for pilgrimage. Even if someone doesn’t have a faith background, there’s something deeply valuable about dedicating a week or two to being in nature, unplugging, and seeking clarity.
This trail—the Via Francigena—has roots going back to the 400s. For many, it was a path to repentance, a sacred journey to Rome. We met people from all over the world. Some weren’t even sure why they were there—they were just searching. Some walk it every year to reflect and release.
Whether it’s climbing a mountain, hiking a long trail, or taking a spiritual retreat, time in creation helps me feel God’s presence. It gives me space to listen, reflect, and be renewed.
This experience has opened our eyes to the possibility of more adventures like this—ones that not only refresh us but potentially serve others too.