Thinking Sideways

How to Think Like a Chess Player and Win at Life

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.

Jennifer Shahade is a two-time U.S. Women’s Chess Champion, author, and professional poker player. She competed on the 2004 U.S. Olympic team that won a silver medal. The first female to win the U.S Junior Open, Jennifer is passionate about empowerment and creative work around the games she loves most: chess and poker. She is a two-time Global Poker Award winner, has appeared on Jeopardy!, and has over 33,000 followers on X. She’s also on Instagram with 14,000 followers. 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 as a spokesperson for women in chess and on topics like The Queen’s Gambit boom in chess popularity. Jennifer lives in Philadelphia.

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Endorsements & Reviews

Early praise for Thinking Sideways:

“Jennifer Shahade is a brilliant, insightful thinker who never fails to entertain and engage. I'm always amazed by the novel approach she's able to bring to any intellectual challenge and discussion. She's even made me want to learn to play chess—something I swore I'd never do. Jennifer is a true role model to any woman who has ever thought about taking on the worlds that have traditionally been branded male.” Maria Konnikova, author of The Biggest Bluff and The Confidence Game