Workday Playdate

283: From Mistakes to Mastery: Career Tips for Bold, Courageous Leaders


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What does it take to leave a prestigious job at Google to chase your true passion?

In this episode of Workday Playdate, Erin sits down with Jenny Wood, the visionary behind Google's Own Your Career program. Jenny candidly shares her transformative journey from a high-powered corporate role to embracing the uncertainties of entrepreneurship.

She delves into the challenges of imposter syndrome, the courage required to be unapologetically selfish in pursuing personal goals, and the art of setting boundaries to maintain a healthy work-life balance. Jenny also introduces her innovative goal-setting framework, 'Rock, Chalk, Talk, Walk,' designed to help individuals clearly define and achieve their aspirations.

Inside This Episode:

  • The pivotal moments that led Jenny to leave Google and follow her passion.
  •  Understanding and overcoming imposter syndrome in professional transitions.
  •  The role of 'wild courage' in embracing one's unique traits and ambitions.
  •  Strategies for setting and maintaining boundaries to protect personal time. 
  • An introduction to the 'Rock, Chalk, Talk, Walk' goal-setting framework.

Who This Episode Is For: Aspiring entrepreneurs, professionals contemplating a career change, and anyone seeking to overcome self-doubt to pursue their true passions. If you're looking for actionable insights on personal growth, boundary setting, and effective goal planning, this episode is a must-listen.

And if you’re interested in taking one small action right now, you can check out our newest freebie, The 5-Minute Team Commitment Reset, here. It’s a plug-and-play exercise that will get your team mentally present, engaged, and committed before any meeting.

No, You Hang Up First (Let’s Keep Connecting)

  • Did today’s episode resonate with you? Leave us a review sharing your favorite insight and we’ll send you a free signed copy of I See You! A Leader’s Guide to Energizing Your Team through Radical Empathy.
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  • Connect with Jenny Wood

    • Jenny’s LinkedIn
  • Jenny’s website
  • Jenny’s book, Wild Courage: Go After What You Want and Get It
  • Jenny’s newsletter
  • Connect with Erin Diehl x improve it!

    • Erin’s website
  • Erin’s Instagram
  • Erin’s TikTok
  • Erin’s LinkedIn
  • improve it!’s website
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  • See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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