Thinking Sideways

How to Think Like a Chess Player and Win at Life

By: Jennifer Shahade

Narrated by: Jennifer Shahade

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.

©2026 Jennifer Shahade

A book of its time

In uncertain times thinking sideways is a powerful tool. We think about our past, we plan our future but after reading thinking sideways, I try to stay more present and see the opportunities around me.

Meh, Not bad but...

Disjointed amalgamation of other books and ideas. Progressive slant permeates the writing. Not terrible but not what I had hoped as an avid chess player and business person.