Episode
Thinking Sideways: Chess, AI, and Smarter Decisions with Jen Shahade
- Podcast
- The James Altucher Show
- Published
- Mar 31, 2026
- Duration seconds
- 3868
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Summary
A Note from James One of my favorite people in the world is back on the podcast: Jen Shahade. She’s been on the show before. She’s a great chess player, a great poker player, a two-time U.S. Women’s Chess Champion, and the author of the new book Thinking Sideways , about how lessons from chess can help with decision-making. As a chess player myself, I can say these techniques really do work. And she even talks about me in the book, which I appreciated. So: how are you going to think sideways? Listen to this podcast. Episode Description James talks with Jen Shahade about what chess and poker can teach us about money, ambition, risk, focus, and decision-making. The conversation starts with income: why salary alone rarely creates real savings, why “big chunks” of money matter more, and why relying on a single job is getting riskier in an AI-shaped economy. From there, they get into one of the core ideas behind Jen’s book: most people think too narrowly. They frame decisions as yes or no, take it or leave it, this city or that city, this job or no job. Jen argues that stronger decision-makers force themselves to find a third option, and often that third option is the one that changes everything. They also talk about career reinvention later in life, how AI can help people learn faster, why chess is such a good training ground for focus, and what it means to stay calm when you’ve already made a mistake and the position has gone bad. The deeper point running through the whole episode is that good decisions rarely come from certainty. They come from staying flexible, thinking in chunks, and continuing to move even when the path isn’t obvious yet. What You’ll Learn Why unexpected “big chunk” income is often more useful for building wealth than salary increases alone. How AI ca…