#091 The art of career transitions with Shiv Choudhury

Most career transitions are treated like cliff jumps.
You quit the job. Burn the bridges. Bet everything on your dream.

Shiv Choudhury chose a different path.

When he left BCG to build a billion-dollar business, he didn’t go all in.
First, he faked an app. It didn’t even work.
But it taught him one thing: customers wanted what he was offering.
That was enough to move to the next stage.

He calls it “pre-to-typing.”
👉 A way to de-risk big moves by testing the most important assumption before you quit your job or raise capital.

Shiv isn’t just theorizing.
He’s lived it — and thrived.

His career spans P&G, BCG, co-founding a fast-growing startup now valued in the hundreds of millions, and launching a successful private equity firm.
Every move was intentional.
Every leap was tested.

In this episode, he gives a masterclass in how to evolve your career — without blowing it up.

He shares:
✅ The “pre-to-type” method for de-risking ideas
✅ Why staying in your job can be the brave thing
✅ His framework for deciding when to prototype, scale, or kill
✅ How a childhood trauma still shapes his risk-taking
✅ Why humility — not hustle — has been his edge

If you’re in a transition — or quietly planning one — this episode is for you.

Episode Shownotes
https://howtolive.life/episode/091-the-art-of-career-transitions-with-Shiv-Choudhury

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