Courtney Joly-Lowdermilk is the founder and lead consultant of the Massachusetts based LLC, Bridge Educational Engineering, where she partners with schools, towns, and organizations to design cultures of belonging that strengthen engagement, performance, and retention. Her career sits at the intersection of education, disability access, and mental health—spanning classroom teaching, student support, and a decade leading college mental-health education. She helped design and build NITEO, a structured leave-and-return pathway for young adults navigating disability and mental-health challenges, and she’s authored practical guidance that makes pausing—and coming back—more humane. She’s partnered with more than 100 teams to shift programs, practices, and policies toward dignity and access. We begin by exploring where Courtney’s energy comes from, meaning that time during elementary school selling popcorn at her grandmother’s bingo hall, or later learning to read a room, and carrying that “be useful” through-line into a career built around people. From there, we head into the deep end: what it actually takes to make belonging operational. Courtney shares the design moves she’s seen turn compliance culture into places where people risk honesty, ask for help, and feel at home. Then we get into the radical idea hiding in plain sight: interruption. What happens when a young person needs to pause—and how do we build the return so it doesn’t become a cliff? Courtney draws from her work with leave-and-reentry pathways to name what makes a pause feel heavy versus what makes it a bridge back. In the second half, Courtney joins us as one of the featured voices in Ted Dintersmith’s new documentary, Multiple Choice. We talk about that simple sign on her office wall—“Work Hard And Be Nice To People”—and the not-so-simple question beneath it: how do families support ambition without becoming “college pushers” or shrinking a kid’s world into a single story of success? We widen the lens to a culture that’s drifted from “fix the schools” to “fix the kids,” and Courtney brings her REACH framework to the role confusion at the center of it. We even dip into the AI urgency narrative—what ticking-clock stories do to teen nervous systems—and what healthier, more human adult moves look like. We close with David Yeager’s 10 to 25 and the mentor mindset—high standards, high support—plus moments that reveal who Courtney is off the page: motherhood, a suitcase note that reads “good luck mommy,” and a shout-out that brings us back to her roots. It’s a conversation about agency, dignity, and designing the conditions for thriving. As always, this show is edited by the very talented Evan Kurohara.