Founders (and leaders) are addicted to solving problems. It’s their crack cocaine.
That’s what startup scaling coach Rob Bier, author of Smooth Scaling and coach to 40+ startups including six unicorns, told me.
And the more I thought about it, the more it made sense.
Fixing things feels good. It proves we’re still valuable. Still sharp. Still in control.

But the addiction comes at a cost.
It blocks us from building teams that solve problems without us.
And it traps us in an old identity—just when we’re ready to grow into something new.

We explore this and more in this episode of the podcast.

Episode Shownotes
https://howtolive.life/episode/092-let-go-to-grow-with-rob-bier

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https://sharadlal.substack.com/

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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

How to Live Newsletter
Go deeper with articles every 2-3 weeks. No spam.
https://sharadlal.substack.com/

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About Sharad Lal
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Which of These 6 Success Traps Is Holding You Back?

After my article on The Success Trap in Esquire resonated with so many, I’ve gone deeper in my latest How to Live podcast.

Working with thousands of senior leaders at Google, Unilever, and HSBC, I’ve identified 6 fear-based identities that block evolution:

🧠 The Solver – Fixes everything, but fears being dispensable → micromanagement
🎯 The Perfectionist – Sets high standards, but fears not being good enough → delays
🔥 The Workhorse – Outworks everyone, but fears not belonging → burnout
😎 The Charmer – Inspires others, but fears rejection → avoids tough decisions
📋 The Taskmaster – Executes efficiently, but fears uncertainty → kills innovation
🌟 The Visionary – Sees the future, but fears irrelevance → never follows through

These identities aren’t weaknesses - they’re strengths turned rigid by fear.
🎙️ Episode 90 explores how to evolve beyond them, without losing what made you successful.

Episode Shownotes
https://howtolive.life/episode/090-the-success-trap-when-success-holds-you-back-with-sharad-lal

How to Live Newsletter
Go deeper with articles every 2-3 weeks. No spam.
https://sharadlal.substack.com/

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https://howtolive.life/contact

About Sharad Lal
https://www.sharadlal.net/

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