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

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🎥 Watch the full episode on Youtube

👯‍♀️ Sisterhood Club - Website

🔗 Connect with Georgie - LinkedIn

Thanks to our sponsor - CH Talent Solutions

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Kate Dillon on LinkedIn

Walk Fearlessly - Programs

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In this episode, I sit down with Kate Dillon, a former lawyer turned entrepreneur, speaker, and advocate for bold career moves. Kate shares her journey from corporate law to founding She Lion, a handbag brand designed for career-driven women, and her evolution into the Walk Fearlessly movement. We dive into the power of taking risks, adapting to change, and future-proofing your career in 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 career
How to navigate uncertainty and build resilience in changing industries
The skills that will set you apart in the future of work (beyond just AI!)
How to embrace failure and turn setbacks into opportunities
Why 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 speaking
04:17 - The unexpected lessons from failing the New York bar exam
19:52 - Why a side hustle makes you a stronger employee
16:26 - The future of work: Portfolio careers & the gig economy
24:32 - Hard skills vs. human skills: What matters more in the AI era?
30:36 - How to shift from a scarcity mindset to an abundance mindset
34:35 - Walking fearlessly: Overcoming fear & taking bold action
43:19 - The role of confidence & why it’s a byproduct of capability
50:14 - Kate’s top career advice for anyone feeling stuck
59:39 - Where to connect with Kate & final thoughts

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