# The Winding Road Show

> A long-form podcast where executives near the end of their careers trace the real path that got them there — not the highlight reel, but the layoffs, wrong turns, and detours that ended up mattering most.

## What the Show Is

The Winding Road is 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.

This is not a tips-and-tactics show. It is not a news show. It is long-form, unhurried, and built more like memoir than interview.

## The Format

- One guest, one conversation. No panel, no crosstalk.
- The same eight questions every episode, so the series builds on itself.
- Reflective pacing — episodes run as long as the story needs.
- New episodes released weekly.

## The Eight Questions

Every guest answers the same eight questions, creating a consistent framework for retrospective across all episodes:
1. Looking back now, what do you understand about that moment that you couldn't see then?
2. What was the detour that ended up mattering most?
3. What did failure teach you that success never could?
4. Who did you become in the hard years?
5. What did you get wrong about what success would feel like?
6. What would you tell the version of yourself still in the middle of it?
7. What do you understand about your own path now that you couldn't have seen at the time?
8. Where did the winding road actually lead?

## Who It's For

Two kinds of listener:
- Executives still chasing the next title or milestone — this show reframes what the road ahead might actually mean
- People in the middle of a wrong turn, a layoff, a hard year — hearing that the detour was the point

## Who Hosts It

Hosted by Brad Habansky. Brad is a sales leader and founder who has spent his career at early-stage B2B SaaS companies. The Winding Road is a separate creative project — a space for the kind of conversation that doesn't fit in a board deck or a GTM plan.

## Category

Long-form retrospective interview podcast. Peers: How I Built This (origin stories), Revisionist History (reframing the past), Armchair Expert (unedited depth). Distinct in its focus on executives specifically and the consistent eight-question framework.

## Contact

- Website: https://thewindingroadshow.com
- Host: Brad Habansky