Day 3: Creative Careers In Crisis with Annie Duke
1h 26m | Jun 25, 2025Annie Duke is an author, speaker, and consultant in the decision-making space, as well as Special Partner focused on Decision Science at First Round Capital Partners, a seed stage venture fund. Annie’s latest book, Quit: The Power of Knowing When to Walk Away, was released in 2022 from Portfolio, a Penguin Random House imprint. Her previous book, Thinking in Bets, is a national bestseller. As a former professional poker player, she has won more than $4 million in tournament poker. During her career, Annie won a World Series of Poker bracelet and is the only woman to have won the World Series of Poker Tournament of Champions and the NBC National Poker Heads-Up Championship. She retired from the game in 2012. Prior to becoming a professional poker player, Annie was awarded a National Science Foundation Fellowship to study Cognitive Psychology at the University of Pennsylvania.
Annie is the co-founder of The Alliance for Decision Education, a non-profit whose mission is to improve lives by empowering students through decision skills education. She is a member of the National Board of After-School All-Stars and the Board of Directors of the Franklin Institute and serves on the board of the Renew Democracy Initiative.
INTERVIEW HIGHLIGHTS:
- Uncertainty creates opportunity for those who embrace it and make decisions anyway.
- Learn how poker is really a game of decision-making under extreme uncertainty
- Hear a simple yet surprising example of how guessing the weight of a dog reveals how we naturally set confidence intervals to make better decisions
- Explore why the sunk cost fallacy keeps us stuck, and how quitting can actually speed up your progress
- Understand how planning across different possible futures helps you prepare for uncertainty instead of fearing it.
- The opportunity hidden in disruption: How to think strategically about your skills and career future
- The emotional cost of closing mental accounts and why quitting challenges more than just logic—it challenges who we are
- How mental time travel helps you step out of the moment and see your decisions with clearer eyes
- Discover how backcasting and premortems help spot early signals—and why an accountability coach can make all the difference
- Quitting isn’t failure—how to rethink the moment you decide to go all in
- Monkeys and pedestals—how to spot the real bottlenecks before wasting time
- Hedging your future by doubling down on the skills that stay the same
RESOURCES:
