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12-15 May 2026
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WOMEN IN TECH GLOBAL CONFERENCE 2025

Jill Stoddard

Founder/CEO at Flexible Communications, LLC

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"Do it Scared: Challenging Outdated and Masculine Ideas About Confidence and Success to Inspire Courageous Leadership"

Thu May 22 - 11:30 AM EDT/New York (See in local time)
Add to Calendar 05/22/2025 11:30 AM 05/22/2025 11:50 AM America/New_York #WTGC2025

"Do it Scared: Challenging Outdated and Masculine Ideas About Confidence and Success to Inspire Courageous Leadership"
#WTGC2025

"Do it Scared: Challenging Outdated and Masculine Ideas About Confidence and Success to Inspire Courageous Leadership"
https://www.womentech.net/ringcentral
https://www.womentech.net/ringcentral
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Session: Do it Scared: Challenging Outdated and Masculine Ideas About Confidence and Success to Inspire Courageous Leadership

"I will ___ as soon as I have more ___ (experience, confidence, skill...)"
This is what I call The Gap Trap: a state of perpetual stagnation caused by our perceived deficits in confidence, skills, or knowledge. We convince ourselves we must first bridge these gaps before taking action—an illusion that keeps us trapped in place, waiting for a perfect moment that never arrives.
In this session, I'll challenge the Gap Trap and other outdated myths about confidence and success. Through evidence-based insights and practical, experiential strategies, we'll explore how to embrace healthy risk-taking and cultivate more courageous leadership, the key to which is willingness to move forward even in the presence of fear, self-doubt, or imposter ‘syndrome.’
At the heart of this talk lies a transformative truth: discomfort isn't a warning sign that something's gone wrong—it's a powerful indicator that we're exactly where we need to be, standing at the intersection of caring and challenge. This is where real growth happens, where leaders emerge, and where our greatest potential awaits.


Key Takeaways

  • Fear and self-doubt are not signals that something is wrong, they are messages that we’re right where we are meant to be -- at the intersection of caring and challenge.
  • The key to success is not confidence: it's willingness to move forward, to take healthy risks, even we are steeped in self-doubt and uncertainty
  • No one lies awake worrying that their favorite series didn't get renewed. They worry about what deeply matters to them. What we fear is what we hold most dear


Bio

Dr. Jill Stoddard is passionate about sharing her expertise in psychology to help women flourish in their work and health. She is an international and TEDx speaker, award-winning former professor, three-time book author, licensed psychologist, coach, and co-host of the Psychologists Off the Clock podcast which is ranked in the top .5% worldwide. Dr. Stoddard is an entrepreneur who founded Flexible Communications, LLC, in Massachusetts, and The Center for Stress and Anxiety Management in California. Her books have been translated into more than a dozen languages and include: The Big Book of ACT Metaphors; Be Mighty; and Imposter No More. Her thoughts have also appeared in the Washington Post, New York Times, Woman’s World, Today.com, Psychology Today, Scary Mommy, Thrive Global, The Good Men Project, Mindful Return, The Boston Globe, and more. She regularly appears on podcasts and as an expert source for various media outlets. She lives in Newburyport, MA with her husband, two kids, and disobedient French Bulldog.

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