In this episode of The Impostor Syndrome Files, we explore why uncertainty feels so uncomfortable for so many of us and how we can build a healthier, more productive relationship with it. My guest this week is Scott Stirrett, author of The Uncertainty Advantage.

Scott shares how his own experiences navigating major career risks, leading a national nonprofit and managing anxiety during the pandemic shaped his thinking about uncertainty. He explains why our brains are wired to fear the unknown, why many people would rather know a bad outcome than face uncertainty and how building “risk-taking muscles” helps us become more resilient over time.

In our conversation, we discuss the concept of anti-fragility, the hidden risks of staying too comfortable and why action is often the best antidote to anxiety. Scott also shares practical strategies for strengthening confidence, including creating a “hype document” to track wins and reconnect those successes to moments of uncertainty and growth. Finally, we explore the impact of AI on the future of work, why learning to learn is becoming one of the most important professional skills and how self-compassion helps us navigate change more effectively.

About My Guest
Scott Stirrett is an entrepreneur, author, and advocate for young people. As Founder and CEO of Venture for Canada, he's raised $80M+ to support entrepreneurial talent, backed by RBC, TD, Scotiabank, and the Government of Canada. His work has been featured in Forbes, The Washington Post, The Globe and Mail, CBC, and BNN Bloomberg. He is also an Ashoka Fellow, former Goldman Sachs analyst, and committed to helping people navigate uncertainty with clarity and compassion.

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Connect with Scott:
Book: https://www.amazon.com/Uncertainty-Advantage-Launching-Career-Change/dp/1459753224
LinkedIn: https://www.linkedin.com/in/scottstirrett/
Website: https://www.scottstirrett.com/ and https://ventureforcanada.ca/
Past podcast appearances: https://open.spotify.com/playlist/1xarZbEJGnncpUs3AlPE4e?si=umdVGEaeRBu_DOrek3ma-A&pi=hqkWxSVGQHyeE

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Connect with Kim and The Impostor Syndrome Files:

Join the free Impostor Syndrome Challenge:
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Learn more about the Leading Humans discussion group:
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Join the Slack channel to learn from, connect with and support other professionals: https://forms.gle/Ts4Vg4Nx4HDnTVUC6

Join the Facebook group:
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Schedule time to speak with Kim Meninger directly about your questions/challenges: https://bookme.name/ExecCareer/strategy-session

Connect on LinkedIn:
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Website:
https://www.kimmeninger.com

In this episode of The Impostor Syndrome Files, we talk about the pressure high achievers put on themselves and the fears that often drive that pressure beneath the surface. My guest this week is Brendan Cournane, attorney, endurance athlete and author of Seeking Serenity.

Brendan shares stories from his decades in law, including the decision to close a major deal on the same day his daughter was born because he feared being seen as unavailable or less committed. He reflects on how stress, expectations and the need to prove ourselves can shape the choices we make at work and in life.

In our conversation, we explore the connection between fear and overachievement, why asking for help feels so difficult for many professionals and how self-awareness helps us respond more intentionally under pressure. Brendan also shares why he believes harmony is a more useful goal than balance. Finally, we discuss the role expectations play in impostor syndrome and why understanding our motives, fears and core values is essential to finding greater clarity, steadiness and fulfillment.

About My Guest
Brendan Cournane is a Certified Professional Coach (CPC) and world-class endurance coach with over 35 years of expertise. After finding his path to recovery in 1989 and discovering the transformative power of running through qualifying for the 100th Boston Marathon in 1995, Brendan learned that mindfulness practice and being true to oneself are integral to achieving happiness and success. He believes and practices the philosophy that “Happiness is a present attitude, not a future condition.”

As Chairperson of the Chicago Bar Association Committee on Lawyer Well-Being and Mindfulness and Co-President of the Mindfulness in the Law Society, Illinois Chapter, Brendan specializes in helping professionals facing stress, transition, and burnout. He has been a training coach for charity marathon teams participating in races around the world, including Chicago, Marine Corps, Disney, Dublin, Rome, Paris, London, Stockholm, Berlin, Tokyo, and Antarctica.

Through his professional development coaching practice, speaking engagements, and training programs, Brendan offers his lived experience, strength, and hope as a catalyst for others seeking to live healthy, fulfilling lives while maintaining balance in even the most challenging times.

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Connect with Brendan:
Website: https://www.coachbrendan.com/
LinkedIn: https://www.linkedin.com/company/brendan-cournane-professional-development-coaching

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Connect with Kim and The Impostor Syndrome Files:

Join the free Impostor Syndrome Challenge:
https://www.kimmeninger.com/challenge

Learn more about the Leading Humans discussion group:
https://www.kimmeninger.com/leadinghumansgroup

Join the Slack channel to learn from, connect with and support other professionals: https://forms.gle/Ts4Vg4Nx4HDnTVUC6

Join the Facebook group:
https://www.facebook.com/groups/leadinghumans

Schedule time to speak with Kim Meninger directly about your questions/challenges: https://bookme.name/ExecCareer/strategy-session

Connect on LinkedIn:
https://www.linkedin.com/in/kimmeninger/

Website:
https://www.kimmeninger.com

In this episode of The Impostor Syndrome Files, we explore how lived experiences shape leadership and influence the way impostor syndrome shows up at work. My guest this week is Natanja Craig-Oquendo, Executive Director of the Boston Women’s Fund. Natanja shares her journey from a childhood grounded in community organizing and allyship to leading mission-driven work focused on social, gender and economic justice. She reflects on how early messages about identity and belonging shaped her sense of what was possible and how those messages continue to influence her inner dialogue today.

In our conversation, we talk about the power of representation, the impact of environment on confidence and how focusing on service can shift attention away from self-doubt. Natanja also introduces the idea of “imprint vs. impact,” reminding us that while impact builds over time, imprint happens in every interaction through how we show up and support others. We also discuss what it takes to lead with honesty and humanity, why creating space for real conversations matters and how to move away from compartmentalization toward more authentic leadership.

About My Guest
Natanja N. Craig-Oquendo is CEO of Boston Women’s Fund, where she is redesigning philanthropy to follow community leadership — not override it. Guided by the principle “do nothing about us without us,” she has spent more than 20 years shifting power toward the communities most impacted by inequity.

Since joining the Fund in 2020, she has tripled grantmaking, expanded partnerships from 6 organizations to 22, grown the operating budget from $300,000 to $2.2 million, and increased the endowment from $2.1 million to $3.5 million. She advanced multi-year grants of up to five years, pioneered a “Request for Conversation” model to replace traditional RFPs with trust-based engagement, and launched the Seed Funding Grant to expand access to capital for Black leaders and grassroots innovators.

She is equally proud of building an organizational culture that supports the full human — where caregiving is not penalized, boundaries are respected, lived experience informs decision-making, and sustainability replaces burnout as the measure of commitment. In 2025, she co-led Carrying the Weight, Leading the Change, a research report developed with UMass Boston, and founded Horizon Collective, a leadership initiative for women and gender-expansive leaders of color.

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Connect with Natanja:
Website: www.bostonwomensfund.org

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Connect with Kim and The Impostor Syndrome Files:

Join the free Impostor Syndrome Challenge:
https://www.kimmeninger.com/challenge

Learn more about the Leading Humans discussion group:
https://www.kimmeninger.com/leadinghumansgroup

Join the Slack channel to learn from, connect with and support other professionals: https://forms.gle/Ts4Vg4Nx4HDnTVUC6

Join the Facebook group:
https://www.facebook.com/groups/leadinghumans

Schedule time to speak with Kim Meninger directly about your questions/challenges: https://bookme.name/ExecCareer/strategy-session

Connect on LinkedIn:
https://www.linkedin.com/in/kimmeninger/

Website:
https://www.kimmeninger.com