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: Subscribe to Amy’s Substack: https://amyduboisbarnett.substack.com/?utm_campaign=profile_chips Follow Amy on Instagram: 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 .

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