Thinking Sideways, Jennifer Shahade
Thinking Sideways, Jennifer Shahade
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Thinking Sideways
How to Think Like a Chess Player and Win at Life

Author: Jennifer Shahade

Narrator: Jennifer Shahade

Unabridged: 6 hr 50 min

Format: Digital Audiobook Download

Publisher: Tantor Media

Published: 04/07/2026

Synopsis

Essential life lessons from the world of chess—from making smarter choices to building focus and confidence—from a former U.S. champion.

Chess is the art of the possible—after all, there are more possible chess moves than atoms in the universe.

Chess players are experts in considering their options, allowing them to seize an opportunity, idea, or move that no one else saw. Two-time U.S. chess champion Jennifer Shahade calls this "thinking sideways." And in today's hyper competitive world, thinking sideways can help you win at life.

In Thinking Sideways, Shahade shows you don't have to be a great chess player to think more like a chess player. From building mind palaces to crafting decision trees, she reveals the most useful strategies from the ancient game that we can use in our daily lives. Drawing on examples from business, sports, and psychology, as well as her own experiences touring the world as a chess and poker player, Shahade transforms our understanding of what success looks like, and how to achieve it for ourselves.

This book is not about playing chess better, or even playing chess at all—it's about how thinking sideways can propel you to success and happiness.

About Jennifer Shahade

Jennifer Shahade is an Olympic chess champion, Woman Grandmaster, poker pro, speaker and author. She is a two-time United States women's chess champion and was the first female to win the US Junior Open. She hosts two award-winning podcasts, The Poker GRID and Ladies Knight. Jennifer works to bring more women, girls and gender minorities into the game through programmes like US Chess Women, the Madwoman's Book Club, and a cross-cultural chess club with girls from all the world, from Kenya to Colombia. She is an ambassador for PokerStars and Poker Power, and a board member of the World Chess Hall of Fame. Her previous books include Chess Bitch (now updated and reissued as Chess Queens) and Play Like a Girl!

Reviews

Goodreads review by Benjamin on March 15, 2026

Very interesting as have not read business : strategy books in a while but I could have had this conferences into a podcast. Take away are memory palaces, preparedness and thinking side away about multiple possibilities from different actions......more

Goodreads review by Talia on February 17, 2026

Thinking Sideways Is basically a class of how to not blunder in Life. Jen once gave me a poker lesson before a big tournament, and the calm, practical advice she shared then is exactly what comes through in this book. She writes about thinking differently when you feel stuck, like in chess when ever......more

Goodreads review by Lisa on April 09, 2026

Thinking Sideways uses chess as a way to understand how the best decision-makers in the world think...and how the rest of us can too. This is a strategy book that's practical. I love her insights on how elite chess players think and how that can apply directly to leadership, business, and life. The f......more

Goodreads review by Sofia on April 21, 2026

I couldn’t put this book down! I rushed through it in two days, wanting the next sentence before finishing the one before it. As a chess player, it gave a clear vocabulary to concepts I’ve always sensed were important but could never quite put into words. However, the most vital takeaway is that this......more

Goodreads review by Brad on April 11, 2026

As a chess fan I loved all the insights into chess culture and thinking in this book, as I expected, but I also enjoyed it for a bunch of other reasons: the range of references to fascinating details drawn from art history, science, sports, high tech, finance, poker, and the author's own life experi......more

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