Why Playing It Safe Is The Biggest Career Mistake – And How to Fix It with Kate Dillon

"Playing it safe is the biggest career mistake—because safe today might be obsolete tomorrow."

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🎥Watch the full episode onYoutube

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🔗Connect with Georgie-LinkedIn

Thanks to our sponsor -CH Talent Solutions

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Kate Dillon onLinkedIn

Walk Fearlessly-Programs

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In this episode, I sit down withKate Dillon, a former lawyer turned entrepreneur, speaker, and advocate for bold career moves. Kate shares her journey from corporate law to foundingShe Lion, a handbag brand designed for career-driven women, and her evolution into theWalk Fearlesslymovement. We dive into the power oftaking risks, adapting to change, and future-proofing your careerin a world shaped by AI and rapid transformation.

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💡What You'll Learn in This Episode:

Why playing it safe could be the biggest mistake in your careerHow to navigate uncertainty and build resilience in changing industriesThe skills that will set you apart in the future of work (beyond just AI!)How to embrace failure and turn setbacks into opportunitiesWhy businesses should rethink side hustles as an asset, not a distraction

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Timestamps:

00:47 - Kate’s career journey: From law to handbags to speaking04:17 - The unexpected lessons from failing the New York bar exam19:52 - Why a side hustle makes you a stronger employee16:26 - The future of work: Portfolio careers & the gig economy24:32 - Hard skills vs. human skills: What matters more in the AI era?30:36 - How to shift from a scarcity mindset to an abundance mindset34:35 - Walking fearlessly: Overcoming fear & taking bold action43:19 - The role of confidence & why it’s a byproduct of capability50:14 - Kate’s top career advice for anyone feeling stuck59:39 - Where to connect with Kate & final thoughts