The James Altucher Show Thinking Sideways: Chess, AI, and Smarter Decisions with Jen Shahade
Jen Shahade, two-time U.S. Women’s Chess Champion, poker player, and author of Thinking Sideways, offers a quick tour of decision-making through chess and AI. Short, sharp takes cover income diversification and why big chunks beat tiny raises. She explains forcing a third option, using AI for late-career upskilling, honing focus with chess-style chunks, and staying resilient after mistakes.
01:04:59
Make Career Changes One Chunk At A Time
- Break big career changes into short chunks and take the first low-cost step now.
- Example: the 47-year-old who studied for the LSAT first, then decided next steps instead of committing five years up front.
Think In Short-Term Chunks Not Final Outcome
- Solve the immediate next problem instead of obsessing about the final outcome to stay flexible and win incrementally.
- Shahade uses chess development examples (knight to d2) to show short-term chunked thinking.
Force A Third Option To Break Binaries
- When stuck between two choices, force a third option to reveal the real preference.
- Shahade's baby-naming example shows a third, offbeat choice (Fabian) cut through a Leo vs Isaac impasse.
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Intro
00:00 • 2min
Diversify income and save with big chunks
02:04 • 1min
Why salary increases rarely create savings
03:07 • 3min
AI: threat, opportunity, and upskilling
06:24 • 2min
Reinventing your career in chunks
08:03 • 2min
Thinking in short-term chess chunks
10:32 • 1min
Computers teach intuition faster
11:41 • 3min
Tradeoffs of early specialization
14:41 • 2min
Mistakes, resilience, and taking risks
16:22 • 2min
Always have three options
18:15 • 3min
House hunting and offbeat third choices
20:52 • 2min
Stanford $5 challenge and reframing problems
23:13 • 4min
Focus as a competitive advantage
26:53 • 5min
Learning new skills with AI and coding
31:58 • 2min
AI increases deep-work but also fatigue
33:52 • 1min
LLMs' limits playing chess and confabulation
35:19 • 4min
Practical coding with AI: vibe coding
39:17 • 3min
Cheating, ambition, and ethical risks
42:40 • 7min
When cheating crosses into harm
49:43 • 6min
Falsification: steelmanning your ideas
56:08 • 3min
Make moves: balance skepticism and action
59:13 • 3min
Push harder in your golden zone
01:02:11 • 2min
Outro
01:04:29 • 29sec
#45724
Play Like a Girl
Jennifer Shahade
Play Like a Girl by Jennifer Shahade is an instructional chess book aimed at encouraging girls to play and learn chess confidently.
Combining clear teaching with stories and illustrations, Shahade provides accessible lessons, strategies, and motivational guidance tailored to young female players.
The book seeks to address gender gaps in chess by offering relatable role models and practical advice to build skill and enthusiasm.
It covers fundamentals as well as mindset topics—helping readers develop both technique and competitive confidence.
The work is part of Shahade's broader advocacy for women in chess through writing and community-building.
#72435
Thinking Sideways
How to Make Smarter Decisions from Chess, AI, and Life (inferred subtitle not stated verbatim in transcript)
Jen Shahade
Jennifer Shahade's Thinking Sideways draws on her experiences as a chess and poker player to teach practical decision-making techniques.
The book emphasizes avoiding binary choices by finding third options, thinking in short chunks, and testing ideas by trying to falsify them.
Shahade weaves personal stories, research, and examples (from chess, poker, and AI) to show how focus, resilience after mistakes, and ambition grounded in values lead to better outcomes.
It also discusses how AI changes learning and work, how to reinvent a career in chunks, and the ethics around cheating and ambition.
Overall, the book provides actionable frameworks for clearer thinking under uncertainty and distraction.
#7
• Mentioned in 501 episodes
Deep Work
Rules for Focused Success in a Distracted World
Cal Newport
In 'Deep Work', Cal Newport argues that the ability to perform deep work—professional activities in a state of distraction-free concentration—is becoming increasingly valuable in our economy.
The book is divided into two parts: the first part explains why deep work is valuable, rare, and meaningful, while the second part presents four rules to transform your mind and habits to support this skill.
These rules include 'Work Deeply', 'Embrace Boredom', 'Quit Social Media', and 'Drain the Shallows'.
Newport provides actionable advice and examples from various successful individuals to help readers master the skill of deep work and achieve groundbreaking results.
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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