How to Beat the Odds: Amy DuBois Barnett on Starting Over, Betting on Yourself, and Winning

#347: In this episode, I’m sitting down with Amy DuBois Barnett — media powerhouse, former Editor-in-Chief, and now author of If I Ruled the World — to talk about what it really looks like to bet on yourself throughout the many chapters of your life, and the importance of being willing to start over at any time. Amy has built a career most people only dream about — from running iconic magazines to leading at the highest levels of media — and then made the boldest move of all: walking away from it to start over as a novelist. This conversation is a masterclass in betting on yourself. We talk about what it takes to trust yourself at the highest level, especially when it doesn’t make logical sense to anyone else. She breaks down her philosophy that fear is actually growth , and why the very things that scare you the most are often the clearest indicators of where you’re meant to go. We also get into something that I think doesn’t get talked about enough: the cost of ambition. What you gain, what you lose, and how to stay connected to yourself while you’re building something big. We talk about timing. About taking years (sometimes decades) to bring something to life, and why that doesn’t mean you’re behind… it means you’re building something with depth. This episode is about self-trust, reinvention, and understanding that betting on yourself isn’t a one-time decision — it’s a mindset you come back to over and over again. This episode is for you if… You’re ready to take a bigger, bolder bet on your life You’re thinking about making a big pivot but it doesn’t “make sense” on paper You’re scared to start over after building something successful You want to trust yourself more but still look for validation from others You’re navigating ambition and questioning what it’s costing you You have a creative idea that won’t leave you alone but haven’t acted on it yet You’re learning how to love all parts of yourself — not just the polished ones Episode Links: Get Amy’s book If I Ruled the World: https://bookshop.org/a/55347/9781250378125 Subscribe to Amy’s Substack: https://amyduboisbarnett.substack.com/?utm_campaign=profile_chips Follow Amy on Instagram: https://www.instagram.com/amyduboisbarnett/ Sponsors: ButcherBox: ButcherBox delivers over 100 premium protein options straight to your door, from grass-fed beef, to wild-caught seafood. Get your choice between free Sirloin Tips, Ground Beef or Chicken Wings in every box for LIFE, PLUS $20 off when you go to butcherbox.com/lucky . Momentous: Momentous Fiber+ is a complete, 3-in-1 formula with soluble fiber, insoluble fiber, and a prebiotic resistant starch. Visit livemomentous.com and use promo code lucky for up to 35% off your first order. Merit Beauty: Merit is a minimalist beauty brand that makes elevated makeup and skincare designed to help you look put together in minutes. Right now, Merit Beauty is offering our listeners their Signature Makeup Bag with your first order at meritbeauty.com . Bask & Lather: Explore viral bestsellers and products of healthier hair of ALL types from Bask and Lather. Go to baskandlatherco.com and use code LUCKY for 20% off. Keep in Touch with Les: Ready to apply what you hear? Subscribe to the She’s So Lucky Newsletter to get weekly episode guides and journal prompts: https://shessolucky.kit.com/newsletter Subscribe to The Lucky Playbook on Substack: https://lesalfred.substack.com/ Follow Les on IG @lesalfred Follow She’s So Lucky on IG @shessoluckypod Follow Les on TikTok @theluckyles Follow She’s So Lucky on TikTok Visit our website at shessoluckypodcast.com This episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct, or indirect financial interest in products, or services referred to in this episode. Produced by Dear Media See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .