Thinking Sideways: Chess, AI, and Smarter Decisions with Jen Shahade

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 can make later-life career changes and self-education more realistic than they used to be.
• Why binary decisions are often traps, and how forcing a third option can clarify what you actually want.
• Why focus is becoming a rarer and more valuable skill in a world built around distraction.
• How strong decision-makers try to disprove their own ideas before committing to them.
• Why mistakes, embarrassment, and bad positions are often signs that you are stretching yourself in the right direction.
• How ambition can become dangerous when it gets disconnected from process and values. 

Timestamped Chapters

• [02:00] Big money in surprising chunks
• Why salary usually gets spent, and why real savings often come from sudden wins.
• [02:16] AI, job security, and choosing yourself
• Why relying on a salary feels shakier now, and how AI changes the equation.
• [03:10] A Note from James
• James introduces Jen and the core idea behind Thinking Sideways.
• [03:49] The book, poker, and having at least three things going on
• Jen talks about the book launch, poker income, and diversified income streams.
• [05:35] Why salary increases don’t create savings
• The psychology of earning more, spending more, and feeling punished by success.
• [08:15] AI as threat and opportunity
• The jobs AI may replace, and the new skills it can help people build.
• [09:42] Reinventing yourself later in life
• A story about becoming a lawyer at 47, one step at a time.
• [12:23] Chess and short-term chunks
• Why good decision-making means solving the next problem, not obsessing over the final outcome.
• [13:31] AI, age, and chess intuition
• How computers changed chess learning, and why experience still matters.
• [17:17] Regret, mistakes, and always having another chance
• How losing positions still teaches resilience and opportunity.
• [20:15] Always have three choices
• Why the best decision often appears only after you stop thinking in binaries.
• [22:20] Buying a house vs. not buying at all
• How being stuck between two options can blind you to the real third option.
• [24:31] The Stanford $5 challenge
• A creativity experiment about reframing the problem instead of solving the obvious one.
• [28:00] Focus as a competitive advantage
• Why being fully locked in matters more than just knowing more.
• [29:22] Deep work in a distracted world
• Why focus is becoming a rare skill and how to protect it.
• [33:16] Learning new skills with AI
• Coding, language learning, and using AI to create personalized practice.
• [35:25] Why AI can feel exhausting
• How AI can keep people in a deep-work state longer than they expect.
• [36:00] Why large language models are bad at chess
• Confabulation, pattern recognition, and what that reveals about AI and learning.
• [44:03] Ambition, values, and cheating
• Why Jen included cheating in a book about decision-making.
• [47:00] Chess cheating, Hans Niemann, and online trust
• The difference between online cheating, live cheating, and the damage done to opponents.
• [57:00] Falsifying your own ideas
• Why stronger players spend more time disproving their moves.
• [01:00:00] Balancing doubt with action
• How to stress-test an idea without freezing yourself.
• [01:02:00] Why ambition matters, even if the first move is crude
• Magnus, scholar’s mate, and why it’s okay to start by trying to win.
• [01:04:00] Work harder when things are going well
• Why success is often the moment to press, not relax.
• [01:04:58] Final thoughts on the book
• James closes on why Thinking Sideways works and what makes it different.

Additional Resources

• Thinking Sideways | Book by Jennifer Shahade
• Home - Jennifer Shahade
• Games and The Grid | Jennifer Shahade | Substack
• Deep Work: Rules for Focused Success in a Distracted World - Cal Newport

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