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Annie shares insights on how grit, often celebrated as a virtue, can also lead to sticking with paths that no longer serve us. Joe and Annie draw parallels to other high-profile figures like Jerry Seinfeld and Will Smith, who chose to step down from projects at the pinnacle of their careers. They also dive into Joe’s decision to retire from the Army. During the episode, Joe and Annie discuss the following topics:

The double-edged nature of grit and its impact on decision-making.
Joe’s personal experience of deciding to retire from the military and the concept of quitting at a high point in one’s career.
The concept of ‘jumping the shark’ and the challenges in identifying the right time to quit.
How to separate your identity from your career
The importance of setting ‘kill criteria’ to effectively determine when to quit under uncertainty.
The role of intuition, sunk costs, and fear of the unknown in decision-making processes.
Using the monkeys and pedestals mental model before starting a major project.

Meet Annie

Annie 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. In 2023 Annie completed her PhD in Cognitive Psychology at UPenn.

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.



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