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

Written By Erin Diehl
 
 
 

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In the latest episode of Workday Playdate, Erin sits down with Jenny Wood, a former Google executive and the founder of the Own Your Career program.  

Jenny’s journey from leading a major operations team at Google to becoming an author and speaker is nothing short of inspiring. She is passionate about helping individuals pursue their goals unapologetically and navigate the challenges of career transitions. 

Trusting Yourself and Embracing Your Weirdness 

During their conversation, Jenny shares the challenges she faced when leaving her stable position at Google to follow her passion for writing and speaking. She emphasizes the importance of trust—both in oneself and in the process of change—and highlights how embracing individuality, or “weirdness,” can be a powerful catalyst for personal and professional growth. 

Overcoming Imposter Syndrome and the Spotlight Effect 

A major theme of the discussion is imposter syndrome—how it sneaks in, convinces high-achievers they aren’t good enough, and holds them back. Jenny shares her own struggles with self-doubt and introduces the spotlight effect, explaining how people often overestimate how much others are paying attention to them. By recognizing this tendency, professionals can start moving past the fear of judgment and self-imposed limitations. 

The Power of Boundaries in Work-Life Balance 

Jenny also stresses the importance of setting boundaries to maintain a healthy work-life balance. She believes that being “brutal” with time is essential for productivity and mental well-being. By clearly defining personal and professional limits, individuals can protect their energy and focus on what truly matters. 

A Goal-Setting Framework for Success 

To help listeners take action, Jenny introduces her goal-setting framework, Rock, Chalk, Talk, Walk. This method encourages individuals to define their goals (Rock), outline necessary steps (Chalk), communicate their intentions (Talk), and take actionable steps toward achieving them (Walk). This structured approach helps transform aspirations into reality. 

Takeaways from Jenny’s Journey 

This episode is packed with powerful insights on trust, courage, setting boundaries, and overcoming imposter syndrome. Jenny’s journey serves as a testament to the power of self-empowerment and taking bold steps toward personal and professional fulfillment.  

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. Use this plug-and-play exercise at the start of any meeting to get your team mentally present, engaged, and committed. 

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

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Connect with Jenny Wood 

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Erin Diehl
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Snack 6: How to Turn Career Mistakes into Growth