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 executives still chasing the next title, the next win, the next milestone — this show sits down with leaders near the end of their careers and traces the real path that got them there. Not the highlight reel. The layoffs, the divorces, the wrong turns, the detours 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.

Ambitious executives, early-to-mid career, still building the version of success they were handed. And 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.

The Framework

Eight questions, every episode.

01

The map you started with

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

02

The detour

The moment — a job loss, a divorce, a health scare — that felt like the worst thing that could happen.

03

The reframe

Looking back now, what do you understand about that moment that you couldn't see then?

04

The thread

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

05

The false peak

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

06

The people

Who showed up during the hardest stretch — and how did that change the direction you took?

07

The letter back

If you could talk to yourself in that moment of setback, what would you tell them?

08

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 threads 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.
  • The same eight questions every time, so the series builds on itself.
  • New episodes released weekly.
Hosted By
Brad Habansky, host of The Winding Road

Brad Habansky

Founder & host of The Winding Road.

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 one is here.

    EPISODE 01 · 46 MIN

    Stephen Kaufman — Syndigo

    First up: 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.

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