Episode 1172: Jennifer Shahade - Thinking Sideways: Chess, Poker & Better Decision-Making

In this episode of The Hidden Why, I sit down with Jennifer Shahade, two-time U.S. Women's Chess Champion, poker pro, author, commentator, and speaker to explore how the mental frameworks behind chess and poker can help us make better decisions and live more intentionally.   Drawing on her new book, Thinking Sideways: How to Think Like a Chess Player and Win at Life, Jennifer shares why great decision-making is less about predicting 10 moves and more about seeing options clearly, adapting quickly, and knowing when to act.   We explore flow, focus, memory, visualization, planning, and why the best thinkers learn to look beyond the obvious move.     Jennifer shares her journey into chess and why she sees it as both a game and an art form. She explains why elite chess players don't simply think "10 moves ahead," but instead focus on seeing the "empty squares" and hidden possibilities. The conversation explores how to balance planning with flexibility and alternative scenarios, as well as why overthinking small decisions can create anxiety and decision fatigue. Jennifer also discusses the role of poker in understanding risk, probability, and uncertainty, and how visualization can support performance under pressure. She highlights the importance of sleep and deep focus, and shares insights on creating your own lane by combining different strengths. Jennifer also defines success as living on your own terms while creating value. Finally, she introduces the SOFA memory framework: Sleep, Organization, Focus, and Active Learning. Key Topics Discussed: Better decisions come from evaluating what matters now, not obsessing over every possible future. Flexibility is a strength. Strong plans leave room for change. The best opportunities are often found in the "empty squares" others overlook. Low-stakes decisions should be made quickly to preserve mental energy for what matters. Memory, focus, and learning remain valuable even in an age of AI and instant information.   About Jennifer Shahade: Jennifer Shahade is a two-time U.S. Women's Chess Champion, professional poker player, author, commentator, and internationally recognised speaker. Her work sits at the intersection of chess, poker, art, culture, and decision-making. She has spoken at organisations and institutions including MIT, Yale, Harvard, NYU, TEDx Baltimore, Boston Consulting Group, and Merrill Lynch. Jennifer is the author of several books, including Chess Queens and her latest, Thinking Sideways: How to Think Like a Chess Player and Win at Life.     Action from This Episode: The next time you're stuck on a decision, ask yourself: "What am I not seeing?" Look beyond the obvious move. Consider the space around the problem, not just the problem itself. Sometimes the best path forward is sideways. Peace, passion, and purpose.   Resources & Links: Get Jennifer Shahade's book on Amazon: Thinking Sideways: How to Think Like a Chess Player and Win at Life     Website: Jennifer Shahade Connect with Jennifer Shahade: Facebook Instagram X