There’s a particular kind of quiet that settles in this time of year. The days get shorter, the calendar fills with holidays, and we find ourselves asking what we actually want the next season to hold.
Our two most recent conversations on the On Adventure Podcast arrived at that question from different directions. One guest has spent years building a family life around shared dreams and calculated risk. The other leads people into the wilderness specifically to strip away the noise. Different trails, but the same thread runs through both: the life we want rarely arrives by waiting for it, and what we choose to leave behind matters as much as what we carry.
Episode 82: Letting Each Other Dream with Brew Davis
Brew Davis is a musician, former schoolteacher, and longtime Appalachian Trail section hiker in Western North Carolina, and one of the few guests to join us a second time.
He tells stories that range from a clean water trip to Fiji, captured in the short film Na Wai, to a father–son trip with his son, Gus, to see Manitoba’s garter snake dens. He also talks about finishing his Appalachian Trail section hike, and about a piece of premarital advice he and his wife have held onto for eighteen years.
What stayed with us is how deliberately Brew and his family have arranged their lives to make room for what matters. “You have to let each other dream,” he says. “That’s life-giving.” Part of what makes that possible is keeping overhead low, because, in his words, “When you have smaller overhead, you’re a lot more nimble.” His other lessons were these: don’t defer the adventures that matter until retirement, and calculated risk beats both recklessness and complacency.
Episode 81: Why We Need the Wilderness — Identity, Purpose & Soul Rest with Todd Pinkston
Todd Pinkston co-founded Wayforward Adventures, a Southern Colorado backpacking organization for adults. He is also the co-author of Unstuck and Alive and is training for his first 100K ultramarathon.
Wayforward trips are built around removing distractions: no phones, no watches, no set schedules. Todd talks about the difference between physical rest and what he calls “soul rest,” and about how the wilderness strips away the personas we maintain at home. One line from the conversation has stuck with us since: “We don’t give ourselves what we actually need. We give ourselves the comfort that we think we want.”
He also left us with a question worth asking more than once a year: “Am I living from my identity or am I living for my identity?” For Todd, purpose isn’t something we find once and file away. It’s something we keep practicing, and sometimes progress means taking things away rather than adding more.
Less Noise, More Room to Dream
Brew keeps his overhead light so his family has room to say yes. Todd removes the noise so people can hear what they actually need. Both point at something we see in financial life all the time: margin is what makes freedom possible.
Margin can take a lot of forms: a spending plan that leaves room for the trip you keep postponing, a reserve that lets you take a calculated risk without betting the house, or a calendar with fewer obligations and more of the people you love. And just as Todd asks whether we’re living from our identity or for it, it’s worth asking whether our money is serving the life we want or simply keeping up appearances. We’re always happy to help you think through that question.
The best plans aren’t the most complicated ones. They’re clear enough that the people inside them can dream out loud, and flexible enough to act on those dreams before “someday” quietly becomes “never.”
