339: Jesse Chaperoned a Trip to Denver

Although we inadvertently took a few weeks off from the podcast, we are back, and overall, the most accurate way to describe life lately is “full.” Between spring breaks, kids popping in and out of the house, and multiple trips layered on top of one another, quiet moments have been pretty rare around here. Listen in this week as Jesse and I do something we hadn’t actually had time to do yet: sit down and process everything that’s happened over the past few weeks. We talk about the whirlwind of travel – his father-son ski trip to Utah with Silas, my church retreat, and, of course, the titular school trip to Denver that Jesse chaperoned, which he describes as “the most servant-oriented trip I’ve been on.” Of course, though, life did not slow down when the trips ended. In fact, we walked straight from the airport into a memorial service for three young men whose lives were tragically cut short. One of them had been very close to our family, and the loss really hit our girls – and all of us – deeply. A big part of this episode, however, as previously mentioned, focuses on Jesse’s time serving alongside students at the Denver Dream Center. Hear how they spent their days hiking in the mountains and their evenings working in inner-city Denver, sharing meals with people experiencing homelessness and connecting with people who were rebuilding their lives after incarceration. Listen as Jesse shares and reflects on some stories about the conversations that happened there such as moments where the goal wasn’t to “fix” anyone but simply to listen, learn names, and recognize the humanity in front of you! Jesse and I also discuss how even just small choices can shape the direction of a life (for better or worse) and how courage often looks like doing something that feels strange, risky, or unsupported. Sometimes, the most meaningful moments come when we step outside the safe little spaces we’ve built for ourselves and choose to do the thing that scares us most. I hope that you enjoy this heartfelt conversation with Jesse! In This Episode [0:35] - We have been absent for a few weeks because of a lot of chaos! [3:45] - Jesse notes how we haven’t recorded since the trips, which became a major part of his story. [4:00] - I reflect on how, after returning home, we attended a tragic memorial before juggling several trips and retreats. [7:26] - Hear how Silas chose a Denver school trip where students hiked Colorado and served the homeless. [10:24] - What is the ultimate goal of the Denver Dream Center? [13:24] - Jesse and I talk about how serving others begins with seeing their humanity, learning their stories, and offering dignity and hope! [16:35] - Serving others ultimately means seeing people’s humanity, learning from them, and connecting without superiority or judgment. [19:33] - I express my belief that experiences such as Silas’s trip help young people rethink priorities and what's truly important. [20:16] - Even small choices and courageous ones can reshape the direction of someone's life. Links & Resources Crystal Paine Social Media Crystal Paine on Instagram (@moneysavingmom) Crystal Paine on Instagram (@crystaliscleaning) Crystal Paine on LinkedIn Crystal Paine on Twitter Crystal Paine on Goodreads Money Saving Mom Money Saving Mom on Facebook Money Saving Mom Deal Seekers Facebook group crystal@moneysavingmom.com Advertising Inquiries:

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339: Jesse Chaperoned a Trip to Denver is an episode from Crystal Paine Show by Crystal Paine.

This episode is 24:39 long.

This episode was published on Mar 24, 2026.

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