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 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