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

by Jennifer Shahade

Essential life lessons and strategy hacks for success from the world of chess, from making smarter choices to building focus and confidence.

You don't have to be a great chess player, to think more like a chess player.

Two-time US chess champion Jennifer Shahade cuts to some of the most important lessons chess can teach you. She shows how the best players consider not just more but better possibilities by thinking sideways, opening our eyes to smarter choices not just on the board but in all areas of our lives.

From building mind palaces to crafting decision trees, Thinking Sideways reveals how to find options that may seem hidden, have confidence in your decisions, feel comfortable going against the grain and maintain deep focus in the face of distraction. Drawing on her own experiences touring the world as a chess champion, as well as fascinating examples from across business, politics, the arts and sports, Shahade transforms our understanding of what success looks like, and how to achieve it for ourselves.

Thinking Sideways proves that games really can make us better versions of ourselves.

Genres: Chess, Nonfiction, Self Help

209 pages, Kindle Edition

Published February 12, 2026

About the author

Thinking Sideways, my new book, is my intellectual hug to readers. You don't have to have things figured out: like a great chess player, it's more important to Think Sideways, and look at all the options, than try to plan ten moves, or ten years ahead.

I am a three-time National Chess Champion--I won the US Women's Championship twice and was the first female to win the US Junior Open. I've also won poker tournaments all over the World from Prague to London to Las Vegas to my hometown Philadelphia.

I'm the author of several books including Chess Bitch / Chess Queens, and my upcoming Thinking Sideways: How to Think Like a Chessplayer and Win at Life.

I'm open to book club invites online, or irl in NYC or Philly--or when I'm on the road :)

Reviews

[Jessica · Rating 5 out of 5]

At once personal and philosophical, Shahade demonstrates both her depth of understanding and her breadth of research. Every chapter gave me exciting ideas for how to teach my chess students more holistically, spending time making them aware of their constant growth by noticing small differences in their thinking or approach, or how to improve my own often stymied decision-making, or how to challenge my perspective. No matter your field, you’ll be more attuned to focus on the process and possibilities.

It’s a book to be savored. Each chapter is beautiful, brilliant, unveiling. I love the connections! The epitome of lateral movement, *Thinking Sideways* removes the fear of failing and reminds us to be open minded.

I have thoughts about each chapter, the intermezzo especially as it reminds us to pause between actions. And about randomness, so often dismissed as meaningless, but yet there is more to life than meaning! For me it’s about flow and connection and change and playfulness. Aside from helping eliminate decision fatigue, randomness is also playful. I think randomizing our routines certainly makes sense. And I wish I could get more sleep and improve my memory! I love thinking about memory palaces, and Shahade’s friends from the poker world or the chess world are all insightful in myriad ways.

I am reminded that it’s one thing to always try to be better as an individual, but as someone who constantly discovers herself fighting ancient, apathetic systems, it’s also “how to *make things* better.” Both are crucial, starting with a change in perspective: can we think and grow in more than one direction, like a knight or a queen? This book does the opposite of gatekeeping. And its positivity in a time of duress for so many is inspiring.

[Benjamin Feasmen · Rating 3 out of 5]

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

[Talia · Rating 5 out of 5]

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 every move looks bad or in poker when the pressure is on and you’re tempted to give up.
Her message is simple but powerful: to slow down look at the position from another angle and don’t let fear make the decision for you. It’s thoughtful and encouraging, exactly like having a strong player in your corner reminding you that there is always a better move if you’re willing to think Sideways. She blends chess strategy with poker psychology, showing how to think in ranges and stay emotionally steady.

[Lisa Sun · Rating 5 out of 5]

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 frameworks here are genuinely useful. The art of the "intermezzo" (the unexpected in-between move that changes everything) is one of my personal favorites. Each one is a tool you'll remember and reach for.

The best leaders are the ones who can see what others can't. This book teaches you how. Whether you've never touched a chess piece or just want to sharpen your edge, Thinking Sideways delivers. Must-read. Full stop.

[Sofia Doroshenko · Rating 5 out of 5]

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 isn't just a "chess book." I can already see these frameworks being a massive asset in my professional life. For anyone with a messy mind who is motivated and self-driven, this book takes your raw talent and provides the lateral thinking needed to reach the next level.

[Brad Buchanan · Rating 5 out of 5]

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 experiences. Jennifer Shahade is not only a terrific, entertaining writer but a genuine polymath. If anyone knows how to think sideways, as well as in every other direction, it's her!

[John Crippen · Rating 3 out of 5]

I met the author last month at a virtual salon hosted by Interintellect and was happy to read her new book. It's a very fast read that gives you lots of good ideas...and makes you want to learn more about chess too!

[Alex M. Bendersky · Rating 5 out of 5]

Good