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

from Career Confidence · host Georgie Hubbard

"Playing it safe is the biggest career mistake—because safe today might be obsolete tomorrow." ___________________________________ 🎥 Watch the full episode on Youtube  👯‍♀️ Sisterhood Club - Website 🔗 Connect with Georgie - LinkedIn  Thanks to our sponsor - CH Talent Solutions  ___________________________________ Kate Dillon on LinkedIn Walk Fearlessly - Programs   ___________________________________ 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.   ___________________________________ 💡 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   ___________________________________ 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

What this episode covers

"Playing it safe is the biggest career mistake—because safe today might be obsolete tomorrow." ___________________________________ 🎥 Watch the full episode on Youtube 👯‍♀️ Sisterhood Club - Website 🔗 Connect with Georgie - LinkedIn Thanks to our sponsor - CH Talent Solutions ___________________________________ Kate Dillon on LinkedIn Walk Fearlessly - Programs ___________________________________ 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. ___________________________________ 💡 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 ___________________________________ 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

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

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This episode is 56 minutes long.

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This episode was published on February 23, 2025.

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