S4E3 - Leader at a Crossroads: From Entrepreneur to Amazon Without Starting Over episode artwork

EPISODE · Feb 16, 2026 · 48 MIN

S4E3 - Leader at a Crossroads: From Entrepreneur to Amazon Without Starting Over

from The Career Transition Podcast · host Nada

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 resumeRashid 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/videoFeel 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/

Episode metadata supplied by the publisher feed · Published Feb 16, 2026

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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 leader...

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S4E3 - Leader at a Crossroads: From Entrepreneur to Amazon Without Starting Over

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