What happens when the very thing that got you to the top — perfectionism, over-preparation, the need to prove yourself in every room — becomes the thing you have to unlearn?

This week on Not All Business, Bridget Winston, a 3x Chief Revenue Officer with over 20 years of experience scaling companies from early-stage disruptors to global brands, gets into all of it. From growing up in all-girls schools to being the only woman in every boardroom, Bridget has built a career by out-preparing everyone around her. But somewhere along the way, she had to start letting that go.

She also went to Italy. Then walked the Camino de Santiago alone. In the rain. Without AirPods. And came back knowing exactly who she was.

Key Takeaways:

• Why the Over-Preparation Habit That Got You Here Might Be Holding You Back

• Imposter Syndrome Is an Environmental Problem (a Hot Take Worth Hearing)

• The "Shrink the Change" Strategy That Works for Teams and for Yourself

• Why Courage Is a Muscle, and the Only Way to Build It Is to Do It Scared

• One-Way Doors vs. Two-Way Doors: How to Stop Treating Every Decision Like It's Final

  
  

Please consider sharing this episode & subscribing to the show for more unfiltered conversations about leadership, growth, and the messy human side of business.

Follow Bridget:

• LinkedIn: https://www.linkedin.com/in/bridgetwinston/

• Instagram: https://www.instagram.com/briwin8

  
  

Links & Mentions:

• Switch: How to Change Things When Change Is Hard by Chip and Dan Heath: https://heathbrothers.com/switch/

• CliftonStrengths (StrengthsFinder): https://www.gallup.com/cliftonstrengths

• Chief — Private Membership Organization for Senior Executive Women: https://chief.com

• Camino de Santiago: https://www.caminodesantiago.gal/en

  
  

Submit Your Sticky Situations & Workplace Dilemmas:

• Got a sticky situation for Not All Business? Send a voice recording to podcast@notall.biz or drop your question in the comments.

  
  

Thank You to Our Sponsors:

• Arcadia Leadership Experience — Three days on a Montana ranch outside Bozeman for senior GTM leaders. July 27–30. Application only.

• https://www.ArcadiaLeadershipExperience.com

  
  

Keep exploring the stories that power Not All Business. Every episode opens the door to fresh insights on what it really means to be a Female Executive or Female CEO, navigating the highs, lows, and unexpected turns of leadership. From real-world workplace dilemmas to candid conversations about breaking barriers, this podcast gives you the tools, inspiration, and perspective to thrive in your own career. So don’t stop here, dive into more episodes, learn from other women in business, and stay connected to the conversations shaping the future of work. Your next breakthrough might be just one episode away. Subscribe for more unfiltered conversations about the messy reality of leadership, professional growth strategies, and the real talk about work with new episodes every week.

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