EP 477- Jennifer Shahade on Cheating, AI, and Thinking Like a Chess Player
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In this episode of Perpetual Chess, host Ben Finegold interviews Jennifer Shahade, two-time U.S. Women's Champion and author of the newly released book *Thinking Sideways: How to Think Like a Chess Player and Win at Life*. The conversation dives deep into the psychology of cheating in chess, drawing on Shahade’s interviews with reformed cheaters who reveal how moral awakenings—like being praised by a grandmaster they didn’t deserve—led them to quit. She explores the tension between process-oriented goals and outcome obsession, using her son’s candid 'MTR' (Medals, Trophies, Ratings) comment as a lens. The discussion expands to memory techniques, advocating for the SOFA method (Sleep, Organizing, Focus, Activating), and challenges the myth of memory palaces for chess, arguing that understanding the logic of openings is more valuable than visualization. Shahade shares her personal experiments with AI, including creating playable online versions of her past games like Hula Chess and Roulette Chess using Claude, framing AI as a creative outlet rather than just a tool. She also reflects on the broader implications of AI in chess and life, emphasizing the 'sandwich method'—using AI only after independent thinking. The episode closes with a heartfelt tribute to Chess in the Schools, Shahade’s first job, and a warning about fake book listings and manipulated reviews on Amazon.
Use the 'sandwich method' with AI: think independently first, use AI to check your work, then think again without AI.
Cheating often stems from hitting a plateau and feeling stuck—reform happens when people realize their actions contradict their values.
Memory in chess is less about palaces and more about understanding the logic of moves and having a deeply internalized board.
AI is a powerful creative tool—build something tangible (like a game) to learn it better than watching videos or taking courses.
Support authentic content by leaving honest reviews—fake books and bot-generated reviews are a growing problem on platforms like Amazon.
Introduction and Context
Host Ben Finegold introduces the episode, notes the recent settlement between Jennifer Shahade and US Chess regarding the Alejandro Ramirez allegations, and outlines upcoming bonus content on the Candidates tournament. He sets the stage for a deep dive into Shahade’s new book, *Thinking Sideways*.
Cheating and the Psychology of Ambition
“It just kind of struck him and he stopped cheating after that moment.”
MTR: Medals, Trophies, Ratings
“I think it's always about balance.”
Memory, Organization, and the SOFA Method
“Two minutes that he saves hunting around for it is two minutes he can save to actually analyze.”
AI as Creative Catalyst
“If you're trying to understand AI better... try to actually make something.”
“When you see a good move, look for a better one.”
“If you're trying to understand AI better... try to actually make something.”
“Use the sandwich method: think with your own brain first, use AI to check, then think again without AI.”
Host
Guest
Jennifer Shahade
person
Ben Finegold
person
Thinking Sideways
book
Claude
other
Chess in the Schools
organization
Danny Ranch
person
AlphaZero
other
DeepMind
organization
Netflix Untold documentary
media
Peter Thiel
person
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