#220 Sihame El Kaouakibi: How to Fail Spectacularly—Then Win Even Bigger – Part Two

Part Two. 

From politics to entrepreneurship, Sihame El Kaouakibi has faced—and conquered—some serious challenges. Burnout? Check. Bankruptcy? Been there. A political storm? Handled. But instead of breaking under pressure, she calls herself “anti-fragile,” using adversity as fuel for reinvention. In Part One, we explore how she built herself back up as a leadership coach, diversity advocate, and creator of Women Leaders OS. And this is just the beginning.

Key Highlights of Our Interview:

Burnt Out, Bankrupt, and Back in Business

“I went from being burnt out, confused, overwhelmed, and even bankrupt to now being in the best shape of my life—physically, mentally, and professionally.”

Validation Detox: Kicking the Need for External Approval

“Without success, without my work, without external validation and recognition, I felt like nothing. I felt nobody.”

Politics 101: When Ego Meets Reality

“I made an ego-driven decision, and it was a messiah complex, believing I had everything—like potential and talents to drive change.”

“I wasn’t aligned with my values and beliefs anymore. So my lesson is if you feel you have to give up on your principles, quit.”

Thriving vs. Surviving: Why “You’re Not Stuck, You’re Just in the Wrong Pot” Applies to Your Career

“The most liberating decision can be to move on and find your tribe, find your environment where you can thrive.”

“Sometimes it’s better to accept the rejection than feeling stuck. Rejection can be redirection, and it’s sometimes better to just leave.”

Operating System for Women Leaders: How to Handle Life’s Curveballs Without Crashing

“My mission is to help 1 million women turn life challenges into life changes for the better. These women want to break through in their careers, but they want to do it without the burnouts.”

“Women still lack internal beliefs and also support systems. So it starts really with women deciding that they are worthy and willing to change.”

Success Isn’t Always Instagram-Pretty: The Ugly Side of the Hustle

“There’s so much about glamorized success, but there is always another side. People you envy might be in deep pain, even if they are millionaires or have social status.”

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Connect with Us:
Host: Vince Chan | Guest: Sihame El Kaouakibi

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--Chief Change Officer--
Change Ambitiously. Outgrow Yourself.

Open a World of Expansive Human Intelligence
for Transformation Gurus, Black Sheep,
Unsung Visionaries & Bold Hearts.

10 Million+ All-Time Downloads.
Reaching 80+ Countries Daily.
Global Top 3% Podcast.
Top 10 US Business.
Top 1 US Careers.

>>>130,000+ are outgrowing. Act Today.<<<

--Chief Change Officer--
Change Ambitiously. Outgrow Yourself.

Open a World of Expansive Human Intelligence
for Transformation Gurus, Black Sheep,
Unsung Visionaries & Bold Hearts.

EdTech Leadership Awards 2025 Finalist.
20 Million+ All-Time Downloads.
80+ Countries Reached Daily.
Global Top 1% Podcast.
Top 5 US Business.
Top 1 US Careers.

>>>180,000+ are outgrowing. Act Today.<<<