A Podcast

The Winding
Road

"It was never a straight line."

Where the detours led.

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    The Premise

    Not the polished version.

    For anyone still chasing the next title, the next win, the next milestone — this show sits down with leaders far enough down the road to look back and see how it all connects, and traces the real path that got them there. Not the highlight reel. The chance conversations, the closed doors, the small turns nobody plans for — the ones that ended up mattering most.

    Inspired by Wayne Dyer's I Can See Clearly Now, every episode is a guided retrospective. A guest looks back across their whole life — work and personal, inseparable — to find the logic hiding inside what once felt like failure.

    The path you're on right now may not be the one you think it is. That's not a problem to fix. It's just how it works.

    Silhouette of a person looking out a window at a city skyline at sunset Every story has a detour
    Aerial view of a coastal road disappearing into morning fog
    Somewhere on the road, the fog lifts.
    Who It's For

    Two kinds of listener.

    Anyone standing in the middle of a setback right now, quietly wondering if it's derailing them — or if it's the thing that ends up mattering most. And ambitious people early in their careers, still building the version of success they were handed.

    The Framework

    Nine threads, every conversation.

    These aren't asked in order, word for word — they're the ground the conversation always ends up covering, because they're what it takes to trace the belief underneath someone's path and help them see it by the end.

    01

    The cold open

    Did you end up where you thought you were going?

    02

    The map you started with

    When you were starting out, what did you think your life was going to look like?

    03

    The hinge

    A small moment that, looking back, reveals something you believed about how life works — even if you couldn't have named it at the time.

    04

    The reframe

    What do you think you're remembering differently now, because you know how the story ended?

    05

    The thread

    Trace a line from that moment to today. What does it connect to? What wouldn't exist without it?

    06

    The false peak

    A goal you reached that mattered less than you thought it would. What did getting there teach you?

    07

    The people

    What was the hardest stretch — and who showed up during it, and how did that change where you ended up?

    08

    The letter back

    If I showed your 22-year-old self a picture of your life today, what would surprise them most?

    09

    The clear view

    Now that you can "see clearly" — what's the pattern you'd tell a 30-year-old you to watch for?

    +

    What's still unresolved

    Not everything needs a bow. Leaving some of it open keeps it honest.

    The Format

    Long-form. Unhurried.
    More memoir than news.

    • One guest, one conversation, no panel, no crosstalk.
    • Reflective pacing — episodes run as long as the story needs.
    • Nine recurring threads, not a script — so every episode covers the same ground without ever feeling like an interview template.
    • New episodes released weekly.
    Hosted By
    Brad Habansky, host of The Winding Road Show

    Brad Habansky

    Founder & host of The Winding Road Show.

    Executive advisor and consultant, drawn to the parts of a career story people usually leave out.

    From the team behind BluebirdGTM — software and consulting for go-to-market teams.
    Be Part Of It

    Know a road worth telling?

    Every guest starts as a name someone believed in. Put yourself forward, or point us to someone whose winding road — the real one, not the highlight reel — deserves an hour.

      Listen

      Episode five is here.

      EPISODE 05 · 56 MIN

      Brian Wagner on the Family You Build

      Brian Wagner grew up in Elmhurst, Illinois, one of four kids raised by a single mom on a Catholic school teacher's salary. When his dad left, his mom's college friends stepped in and became family. We talk about walking business parks selling phone systems for $14,400 a year, the night his wife called him out for playing politics at AT&T, and the long runs at Oracle, Salesforce and CloudCraze built on the people around him, not the deals.

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