The Winding Road Show

Brad Habansky
  • 5.0 (1)
  • Careers

There are no wrong roads to anywhere. Wayne Dyer wrote that, and it's the idea behind The Winding Road Show. Each episode, host Brad Habansky sits down with an executive — someone far enough down the road to look back — and traces how the twists and turns of their career and personal life actually connect. Not the highlight reel. The chance conversations, the closed doors, the small turns nobody plans for — the ones that ended up mattering most. It's for anyone standing in the middle of a setback right now, wondering if it's derailing them or if it's the thing that ends up mattering most. And for anyone early in their career, still building the version of success they were handed. Long-form, one guest, no script. New episodes weekly.

Episodes

  1. Oct 28

    Cathy Highley: The Foundation

    Cathy Highley went to college certain she’d be an accountant. Then a required programming class changed everything. Forty years later, she’s spent her whole career in technology without ever leaving central Illinois: fourteen years at Illinois Power and nearly twenty at ADM, where she’s an enterprise architect. Along the way, she married her high school sweetheart, raised three kids, and turned down a move to St. Louis to keep her family rooted in Decatur. Ask Cathy about any of it and she credits the team, the smart people, the leaders who let them run. This conversation is about why the people holding everything up rarely see it in themselves. In this episode: The required class that changed the direction of her careerPlaying piano by ear and the surprising connection to programmingBeing a woman in IT in the ’80s and ’90s, including a job interview at eight months pregnantChoosing family over a move to St. LouisFinally becoming a manager, then choosing impactful work over the titleBuilding standards and guardrails so others can build on top of themThere are no wrong roads to anywhere.

  2. Oct 4

    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. Brian has been building that kind of family ever since. In this episode, Brian talks 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 quitting over dinner in front of his boss. He also covers the long runs at Oracle, Salesforce and Cloud Craze that were built on the people around him, not the deals. The Winding Road is a show for executives looking back at the real path that got them there. Not the highlight reel, but the detours, setbacks and reframes that ended up mattering most. Inspired by Wayne Dyer's I Can See Clearly Now.

  3. Sep 23

    Ron Knauer on There is Always Something to Prove

    Ron Knauer grew up in a small Indiana town, in a family where no one had gone to college. When more than 70 people applied for an entry-level job at IBM, Ron knew he probably wasn’t the best candidate on paper. So he found another way to stand out. That instinct followed him for the next four decades. Ron went from painting parking lot lines at night to building a career in enterprise sales, eventually working on deals worth hundreds of millions of dollars. But underneath the success was something that never really went away: a chip on his shoulder and a need to keep proving himself. In this episode of The Winding Road Show, Ron looks back at where that drive came from, how it shaped the way he sold and led, the life-changing deal that changed what was possible for his family, and what all those years of chasing the next win look like from the other side. As Ron puts it: “Why do the same when you can be different and win more?”

  4. Sep 16

    John Mattingly on The Goal Line that never Arrives

    John Mattingly took over his family's construction business from his father, grew it from a dozen employees to nearly 600, and built it through the 2008 housing crash that wiped out most of his competitors. By any outside measure, he's made it. In this episode, John talks about walking away from a promising path in law to join the family business, what actually happened between him and his dad along the way, and the cost of chasing a goal line that keeps moving — $12 million, then $15 million, then $25 million, then $50 million, and never quite "enough." He's honest about what freedom really means once you own something instead of working for someone else, and what he'd tell himself now about slowing down enough to notice it. The Winding Road is a show for executives near the end of their careers, looking back at the real path that got them there — not the highlight reel, but the detours, setbacks, and reframes that ended up mattering most. Inspired by Wayne Dyer's I Can See Clearly Now.

  5. Sep 9

    Udo Rauch on the Career You Could Have Never Planned

    Udo Rauch studied physics before building a thirty-year career across technology, enterprise sales, and leadership. Almost none of it went according to plan. In Episode 2 of The Winding Road Show, I sat down with Udo to talk about the opportunities he never expected, the fear of failure that keeps people from taking a different road, and why trying to control every part of your career doesn't work. We also talked about the motorcycle accident that changed how he viewed his life, his decision to take a year away from business, learning to play Chopin, getting married and having a daughter later in life, and the Elton John story that shaped his attitude toward failure. Udo Rauch on the Career You Could Never Have Planned

  6. Sep 3

    Stephen Kaufman on the Detours That Built a Career

    Stephen Kaufman, Chief Strategy and Alliances Officer at Syndigo — a guy who almost became a lawyer like his dad, ended up teaching Macintosh graphics to union print workers, and built a company he sold for over $100 million. We talk about the calls, tips, and chance conversations that kept opening doors he never planned for — and why he's spent his life learning to notice them.

  • 6 Episodes

About

There are no wrong roads to anywhere. Wayne Dyer wrote that, and it's the idea behind The Winding Road Show. Each episode, host Brad Habansky sits down with an executive — someone far enough down the road to look back — and traces how the twists and turns of their career and personal life actually connect. Not the highlight reel. The chance conversations, the closed doors, the small turns nobody plans for — the ones that ended up mattering most. It's for anyone standing in the middle of a setback right now, wondering if it's derailing them or if it's the thing that ends up mattering most. And for anyone early in their career, still building the version of success they were handed. Long-form, one guest, no script. New episodes weekly.

Information

  • Creator
    Brad Habansky
  • Years Active
    2026
  • Episodes
    6
  • Rating
    Explicit
  • Copyright
    © 2026 Brad Habansky
  • Show Website
    The Winding Road Show