The Value of Open-Ended Travel
I woke up to soft music and morning stillness at the Cloran Mansion Bed and Breakfast in Galena, Illinois. With a couple hours to spare before breakfast, I sat with my first cup of coffee and reflected on a travel habit I’ve grown to love: leaving room in the schedule to pivot.
While I always book my first and last nights in advance — in this case, Galena and Chicago — I intentionally leave the middle of my trip open. Not unplanned … just flexible. That openness allows the trip itself to guide me. Each night, I look over my map, my notes, and my new discoveries, and I adjust. I course correct. It’s travel with intention … but also curiosity.
Just yesterday, I chatted with the innkeeper here and learned about a Midwest association of charming B&Bs, many of which don’t show up on the big booking sites. That conversation revealed new gems in Wisconsin and Minnesota I would have never found otherwise. And if I had booked everything rigidly in advance? I’d have missed that chance.
Meeting Paul, the Innkeeper Who Took a Leap
Galena is full of stories. You can feel them in the cobblestone streets, the 19th-century buildings, and the view over the Mississippi River. But one story I had the pleasure to document was more personal … the journey of Paul, the innkeeper of the Cloran Mansion.
Once a high school teacher and department chair in the Chicago suburbs, Paul made a major life pivot later in life. After 26 years in education, mostly teaching U.S. History and Government, he and his wife decided to chase something different, something warmer, more personal, more rooted in hospitality.
What drew me to Paul wasn’t just his career change, it was how he approached it. Instead of leaping blindly, he immersed himself. He volunteered at the inn over winter breaks. He shadowed the previous owners. He dipped his toes into a new world before taking the plunge.
In our conversation, he shared something that stuck with me:
“Who you were at 22 is not necessarily who you are at 50. And that’s okay. If money isn’t your only motivation, you give yourself room to try something else… something meaningful.”
Paul now runs the inn full-time. He hosts guests not out of obligation, but by choice. And he offers them a space to reset and reconnect, just as he once did for himself.
Pivoting at Any Age
His story resonated with me because, in many ways, it mirrors my own. The “50 at 60” journey I’m on is a pivot: a step away from a successful but intense life in event lighting, toward something slower, more story-driven. It’s a chapter where I’m chasing light in new ways: through photography, video, travel, and conversation.
If you’re reading this and thinking about your own pivot … maybe Paul’s story is your sign.
Closing Out Galena
I probably should have filmed a more formal closing shot down by the river or in the vibrant downtown. But life doesn’t always need a perfect wrap-up. Sometimes a quiet journal entry with coffee will do.
Galena has been a gem, and Paul’s story was the perfect way to launch this chapter of my trip. I’m off to Pella, Iowa next, and I can’t help but wonder … who else will I meet who’s walking a new path?
Thanks again, Paul. Here’s to first interviews … and second acts.
