The Winding Road: What Six Journeys Taught Us About Finding Your Way
There’s a question I ask almost every guest on the Path Found podcast: Did you plan this?
The answer, almost without exception, is no.
Episode 36 is a little different from our usual format. Instead of a single conversation, I went back into the archive and wove together moments from six people who have been guests on this show and who have each, in their own way, had to abandon the plan and figure it out as they went.
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Path Found is the podcast for anyone who’s ever asked, “What now?”
This show explores the real, messy, and inspiring journeys people take to find fulfilling work—and themselves. From pivots and side hustles to mentorship and major career changes, Path Found reveals what college never taught and counselors never said.
What if the idea of a “dream school” is shaping college decisions in all the wrong ways?
In this episode of Path Found, I sit down with New York Times' bestselling author and journalist Jeffrey Selingo to unpack how students and families navigate one of the most consequential and misunderstood decisions of their lives. Drawing from his books There Is Life After College, Who Gets In and Why, and Dream School, Jeffrey explains why we put too much pressure on picking majors early, how prestige and rankings distort choice, and why most careers are built through skills, adaptability, and relationships rather than linear paths.
We talk about the changing early‑career job market, the impact of AI, the importance of mentorship and belonging, and why many less‑selective institutions may actually prepare students better for the real world. This conversation is essential listening for students, parents, educators, and anyone questioning whether the traditional college narrative still serves today’s generation.
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What I found when I listened back surprised me. Across wildly different industries, backgrounds, and timelines, the same two truths kept surfacing:
There is no single right path. And you cannot find it alone.
Who You'll Hear From
This episode draws from conversations with:
- David Camarena (Episode 1) — on starting over and building something new when the original road closes
- Coach Christian (Episode 2) — on learning to lead yourself before you can lead anyone else
- Michael Harley (Episode 3) — on the unexpected clarity that comes from knowing what you don't want
- Taylor Rabe (Episode 4) — on what it actually looks like to pivot mid-career without a safety net
- John Sayers (Episode 7) — on the mentors who showed up at exactly the right moment
- Sierra Emrick (Episode 11) — on giving yourself grace when the path looks nothing like you imagined
What This Episode Is About
We talk a lot at Keystone Network about non-linear paths and about the gap between what students think a career is supposed to look like and what it actually looks like once you’re living it. This episode is, in many ways, the audio version of that conversation.
The detours weren’t detours. The pivots weren’t failures. The moments where things fell apart were, for every single one of these guests, the moments that mattered most.
“There’s something you know for sure you don’t want. So maybe start there.”
One of my favorite lines in this episode comes from Michael Harley, who compared finding career clarity to standing at a vending machine: “There’s something you know for sure you don’t want. So maybe start there.”
That’s the kind of practical, human wisdom that doesn’t show up in a career center brochure, and it’s exactly why these conversations exist.
Stream Episode 36 on your favorite platform
If this episode resonates with you, share it with a student, a mentee, or someone you know who’s in the middle of figuring it out. That’s what Path Found is for.
