Have you ever noticed your life getting smaller without ever deciding to shrink it? Not all at once. Just one canceled plan, one closed door, one quiet no to something that used to feel possible, until one day you look up and wonder where all the room went. That's where Scott Stirrett found himself partway through COVID. He'd already done the hard things once. Left a steady job at twenty-two to start a charity from nothing. Came out, eventually, after years of being afraid of what people might think. But comfort, real comfort, has a way of quietly wearing off if you let it. A decade of stability dulled the muscle he used to take risks with, and it took a pandemic and a therapist's gentle observation to show him how far it had drifted. This is a conversation about what it actually takes to rebuild a relationship with the unknown. Not white knuckling through it. Practicing it, on purpose, the same way you'd train a muscle you forgot you had. And about what becomes possible once you stop needing to know how things will turn out before you're willing to try. What You'll Hear: How a decade of stability quietly wore down Scott's comfort with risk The moment in COVID that made him name his own perfectionism out loud Why he believes self compassion, not ambition, is the real engine behind growth What it took to leave the charity he built and led for twelve years How coming out later in life changed his relationship with fear itself The difference between a good decision and a good outcome, and why that distinction matters Guest Bio: Scott Stirrett is a Canadian entrepreneur, author, and social impact leader whose mission is to help people reach their full potential. He is the Founder of Venture for Canada (VFC), a national charity that has supported over 10,000 young professionals since its launch in 2013. Under Scott’s leadership, VFC has raised over $80 million and built partnerships with organizations including Employment and Social Development Canada, RBC Foundation, TD Bank, Scotiabank, and leading Canadian foundations. The organization focuses on equipping early-career Canadians with the entrepreneurial skills and mindset needed to thrive in an uncertain economy. Scott is the author of The Uncertainty Advantage, a practical guide for young professionals navigating today’s unpredictable world of work. Endorsed by Andrew Yang, Stephen Poloz, Amanda Lang, Eric Ries, Sukhinder Singh Cassidy, and Michele Romanow, the book draws on lessons from scaling VFC, emphasizing adaptability, entrepreneurial thinking, and lifelong learning. Before founding VFC, Scott worked at Goldman Sachs in New York City. He is a graduate of Georgetown University’s Walsh School of Foreign Service. He has been recognized as a Telus LGBTQ Innovator of the Year, an Action Canada Fellow, a Globe and Mail Changemaker, and an Ashoka Fellow, among other honours. His commentary has been featured in The Washington Post, Forbes, Fast Company, The Globe and Mail, CBC News Network, and BNN Bloomberg. He currently serves as Co-Chair of the Board at the Canadian Centre for Housing Rights and sits on the Board of the Speech and Debate Canada Foundation. Links: Personal website: https://www.scottstirrett.com/ LinkedIn: https://www.linkedin.com/in/scottstirrett/ Instagram: https://www.instagram.com/scottstirrett/ Substack: https://substack.com/@scottstirrett Amazon: https://www.amazon.com/Uncertainty-Advantage-Launching-Career-Change-ebook/dp/B0DGCD6ZCV/ —- Listen and follow: www.thelifeshiftpodcast.com/follow Subscribe to the newsletter: https://thelifeshiftpodcast.beehiiv.com/ --- comfort with uncertainty, fear of the unknown, perfectionism recovery, coming out later in life, leaving what you built, self compassion practice, risk taking and growth, shrinking under pressure, rebuilding confidence, chosen family and friendship Learn more about your ad choices. Visit megaphone.fm/adchoices
