Thinking Sideways: How to Think Like a Chess Player and Win at Life

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.

Author: Jennifer Shahade
Publisher: Pegasus Books
Published: 04/07/2026
Pages: 272
Binding Type: Hardcover
Weight: 0.90lbs
Size: 9.14h x 5.99w x 1.11d
ISBN: 9798897100729


Review Citation(s):
Library Journal 11/14/2025 pg. 1

About the Author
Jennifer Shahade is a chess and poker champion, author and speaker. The first woman to win the U.S. Junior Open, she also holds two U.S. Women's Championship titles. She is passionate about building life skills and creative work around the games she loves most: chess and poker. A two-time Global Poker Award winner and silver Olympic medalist, she has appeared on Jeopardy! and her writing has appeared in The Washington Post, The Wall Street Journal, and The New York Times. She is featured regularly on major news outlets, including CNN and NBC, commenting on topics such as the chess boom sparked by The Queen's Gambit. Jennifer lives in Philadelphia.