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.

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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