The Career Transition Podcast

Leader at a Crossroads: From Entrepreneur to Amazon Without Starting Over


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After 10 years of building successful businesses, Rashid hit a moment most senior leaders never admit:

He looked around at his peers getting promoted, buying houses, building stability…

And wondered if he’d made the wrong bet.

In this episode, we unpack what it really takes to navigate a senior career pivot, especially in today’s market.

We talk about:

• The identity shock of feeling “behind” after a decade of success
• Why entrepreneurial experience is hard to translate into corporate leadership
• The mindset shifts required to transition strategically (not emotionally)
• The qualities senior professionals need to compete in this market
• Why accountability and positioning matter more than rewriting your resume

Rashid went from running his own ventures to landing at Amazon across countries without starting over.

If you’re 15+ years into your career and questioning your next move, this conversation will help you think clearly before you act impulsively.

If you’d like help navigating your own crossroads, book a Career Strategy Call using this link: https://go.nadabuhendi.com/video

Feel free to connect with me on LinkedIn and share with me your feedback about this episode. I always love hearing from my listeners: https://www.linkedin.com/in/nadabuhendi/

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The Career Transition PodcastBy Nada