The map you started with
When you were starting out, what did you think success was going to look like?
"It was never a straight line."
Where the detours led.
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.
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.
When you were starting out, what did you think success was going to look like?
The moment — a job loss, a divorce, a health scare — that felt like the worst thing that could happen.
Looking back now, what do you understand about that moment that you couldn't see then?
Trace a line from that moment to today. What does it connect to? What wouldn't exist without it?
A goal you reached that mattered less than you thought it would. What did getting there teach you?
Who showed up during the hardest stretch — and how did that change the direction you took?
If you could talk to yourself in that moment of setback, what would you tell them?
Now that you can "see clearly" — what's the pattern you'd tell a 30-year-old you to watch for?
Not everything needs a bow. Leaving some threads open keeps it honest.
Founder & host of The Winding Road.
Executive advisor and consultant, drawn to the parts of a career story people usually leave out.
One email, when episode one is live. Nothing else.