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, Audiobook, Personal Development

272 pages, Hardcover

Published April 7, 2026

About the author

As a chess and poker champion, it's my goal to make your life better through games, even if you don't play yourself.

Thinking Sideways, my new book, is my intellectual hug to readers, and honestly, a book I wrote for myself first. Since finishing it, I've been on a roll. I had my best year in poker ever and became the first ever ambassador for US Chess, after resolving a years-long battle where I spoke up for victims of assault and abuse.

The key point is this: 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 to plan ten moves, or ten years, ahead.

In Thinking Sideways, I'll help you sharpen your memory and make faster decisions. I also write about these topics on my Substack, See The Sideways Move.

I'm open to book club invites, online, or in person 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.

[Christopher M · Rating 5 out of 5]

Thinking Sideways by Jennifer Shahade, 2026, Pegasus Books 272pp

First of all, two disclosures. I was sent a copy of the book by the author (I have since purchased other copies for friends), and I have known Jen for several years. I strive mightily to show no bias in any reviews I do, but I’m aiming for full transparency here.

Back in 2023, when she released Play Like a Champion, her book, a natural, expanded follow-up to her prior book Play Like a Girl, in the same way that Chess Queens was the natural successor to Chess Bitch, Jennifer did some pretty typical promotional interviews. I believe it was on an episode of Ben Johnson’s podcast, Perpetual Chess, where I first heard her mention that she was getting ready to embark on a far more ambitious type of book.

The way she hinted at the topics that this mysterious project would entail was alluring in the same way that when you look at photos of the first Hollywood Stars, you can see something there, even if you can’t quite tell what.

Over the next couple of years, whenever I heard a reference to this project, I would be intrigued all over again. Especially as I began to piece together that this book wouldn’t be about improving at games such as chess or poker in the traditional sense. Instead, the book would be about how to approach the thinking part of the improvement process from a whole new direction.

Here is the copy of the North American Edition. The cover in my banner above is from the UK Edition, which is the version I own.

Let’s open the pages.

The book is composed of seven chapters and a conclusion. The chapters are:

Decision Trees

Time Management

Memory

Pattern Recognition

Ambition

Know Your Strengths

Taking Risks

Reading this book will take you on a journey of thinking. Not just thinking in straight lines, but thinking sideways. The idea is that if you want to solve a problem, you should approach it from every possible angle. When the direct approach stalls or fails, there may be a side alley you can try.

Rather than comparing the various chapters to one another to draw parallels and conclusions, I prefer to give the reader an overview of what has really stuck with me. Unlike many books, I didn’t read this one over the course of a couple of days. Instead, I sat down and read the first half quickly, then life got in the way.

Once I got things back on track, I started slowly reading through and absorbing some lessons from the books while taking some notes that now form the basis of this review. So, rather than trying to quickly assimilate and then regurgitate what I have learned, as is the historical tradition of most book reviews I have done, I was able to really mull over many of the concepts and lessons.

Tunneling

One concept that really resonated with me was the idea of “tunneling” as it relates to candles. If you are into candles like I am, then you are familiar with this concept, even if you didn’t know the name.
Tunneling is when you light a candle, let it burn for only a short time, then extinguish it. Since you didn’t let it burn for long, the wax didn’t melt evenly across the surface. Without addressing this, you will not use all the wax in the candle before the wick is gone.

When it comes to learning or training, it’s easy to see the equivalents of tunneling. Let’s say you are working to improve at chess. You know you need to analyze your games. So you start to analyze one. You start playing through the opening, and then you get distracted when you realize you were meaning to look up this opening after the game, but hadn’t done so yet.

So you open Chessbase, and you start clicking through the moves of the opening. Then you realize that a Chessbase database can give you the moves, but not the ideas behind them. So you go to grab that book on the Petroff from your bookshelf.

You start working through the first line, but then you realize the book is from 2013, so you log in to Chessable and buy that new course. At this point, you’ve lit several candles, but you haven’t allowed any of them to burn evenly before moving on to lighting the next. Therefore, what have you really learned? You started out determined to improve by analyzing one of your games, and an hour later, you’re in the quick starter of some Lifetime Repertoire. At no point did you actually start working on the analysis.

I can tell you from personal experience that merely being aware of the concept of tunneling has led me to be far more aware of the need to give training sessions enough time to

Sleep

This one also resonates with me very deeply on a personal level. In the past 2-3 years, I have lost close to 90 pounds. A question I am frequently asked is some variant of “what is your secret?”

What people seem to want to hear is some complicated explanation involving multiple types of highly marketed diet plans (Oh, are you on Atkins/Zone/South Beach/Paleo/etc?) was a very common inquiry.)

Nope. The answer devolves to one thing. Sleep.

While it’s a bit more complex under the surface, on the surface, it’s really that simple. I have lost a lot of weight over the past few years simply by sleeping more. More sleep has reduced the temptation to reach for high-energy foods and drinks that are just sugar and caffeine, leading to less consumption of those things. That has led to more natural energy, which in and of itself reduces the feeling that you need those things to get through the day.

Perhaps, unlike me, you do not need to lose weight for health reasons. Perhaps a goal you are focused on is career advancement. In a case such as this, you might find that more sleep leads to increased ability to stay attentive during meetings. As you pay closer attention, you will have more opportunities to respond to requests for input or suggestions. This may lead your boss to notice you more and develop a higher opinion of your value.

Whatever your goals are, more sleep is far more likely to help than hinder.

Memory

I am someone who grew up with an incredible working memory. I am also someone who was then very actively engaged in behaviors that really hampered my formerly incredible memory.

In Thinking Sideways, one of the subjects Jen interviews is Yanjaa Wintersoul, a former World Memory Champion. Yanjaa explains memory techniques involving crafting stories around the things you want to remember.

An anecdote Jennifer gives in the book is about trying to remember Sarah and Michael, Ellie's parents. So you may use the word “smelly” to remind you that Sarah and Michael are Ellie’s parents.

LLMs

Here is one area in which I wish my notes were better. At one point in the book, Jen dives into some common ways of thinking about LLMs. The term LLM typically refers to a Large Language Model, such as Claude or ChatGPT, trained on massive text datasets to understand, summarize, translate, and generate human-like language.

I have seen a lot of handwringing around LLMs recently, and I’ve done my fair share of it as well. Then, I read Thinking Sideways and gained some insight, which has led to some new hope.

We’ve aleady experienced the invasion of AI into the chess world in the form of engines. One of the fears when engines were introduced and became strong was that they would kill the game. Instead, what changed was the approach to openings and preparation. It broadened the game rather than destroying it.

So perhaps there’s a lot of Chicken Little going around here as well. Listen to Jennifer, we very well may be overreacting here.

Round Number Bias

This is a big one in the chess world since we all have a number associated with our name that frequently changes. Sometimes, though, chasing that round number can do more harm than good.

I know someone in Wisconsin who almost made Master. Within a point or two. I didn’t know him when he achieved that rating, so I may be missing some details, but the bigger point remains.

He decided that when he got close to 2200, he would control the events he would play to get him to the promised land. Many of us have seen this in some form or another over the years. Enter a tournament, crush someone outrated by hundreds of points in round one, then drop out and gain one point, and try to do it again two more times.

Well, something happened, and he didn’t make it. Eventually, he quit playing classical rated events altogether, and the lack of rapid and blitz events in general led him to ride off into the sunset.

I know another guy who made 2199. I haven’t asked if he ever tried to control for the events he played to get that final elusive point, but I do know that he’s still an active player today, so clearly, he didn’t let a round number bias hold him back too long, if at all.

How can you apply this in your life? Let’s say you are trying to get your weight under a certain mark. I’ll use 300 pounds since that was a number I had to fight to get below. You work and work. You’re losing weight and making progress. You are determined to be under this weight before you leave for vacation on a specific date. The day comes, and you step on the scale… 300.1.

OK, you didn’t make the goal, but you barely missed it. The margin is so small that, from a practical sense, there is no difference.

You now have two choices, each leading to its own path forward. Choice one. Embrace the fact that you have essentially made it, and know that if you keep working as hard as you have been, the next time you step on that scale, you are likely to have reached your goal weight, even if not in your preferred timeframe.

Choice two is to feel like a failure and accept the increased risk of backsliding into the same behaviors you are trying to avoid.

One choice feeds the success that brought you this far, while the other may feed the demons that had you on the wrong path in the first place.

Think sideways. Don’t let that bias get you.

Cheating

Wow, did this one resonate with me. Most people reading this probably experienced some form of cheating during the pandemic. Few probably experienced it the way I did.

My company, the International Academy of Chess (I didn’t select the name; I inherited it, so don’t hate me!), was running rated scholastic events online during the pandemic. While the overall number of cheaters was low, they had a disproportionate impact on the final standings, since they usually finished in the top trophies if they cheated enough.

I just checked, and we ran 91 online events, so, sadly, we became very well aware of the cheating epidemic.

Each week, after fair play was complete, we would invite players suspected of cheating to an interview. The guy who was conducting the interview (born in the USSR - you can’t make this up) was really good at them, and the kids would almost always wind up confessing.

Upon confession, we would walk them through how we would allow them to rehabilitate and play in future events. With only one or two exceptions (I can’t recall if it was precisely one, there may have been a second), every one of these kids who were given a second chance played honestly going forward.

This is an important backstory because Jennifer mentions that while kids are much more likely to cheat in any given endeavor, they are also more likely to give up cheating sooner.

To me, the real lesson here is to ask oneself who the real villain is. The eight-year-old kid who once broke down sobbing in one of our interviews, saying he just wanted to make his mom proud by winning a trophy, or the 48-year-old adult who thinks that kid should be banned for life.

If you think cheating is just a simple black-and-white issue, I’d like to point out that I learned to think sideways about topics such as cheating, and you can too.

What’s Your Chess Boxing?

For those who aren’t familiar with chess boxing, it’s exactly what you think it is. It starts with a round of chess, which I believe lasts four minutes. When the chess round ends, the board, pieces, and clock are carried out of the ring, and a one-minute round of boxing begins.

What a concept. Jen talks about the genesis of chess boxing and encourages readers to find their own chess boxing. In this case, a metaphor of taking two things that you might not be the best at individually, but when combined, perhaps you are among the world's elite.

Jennifer talks about her invention combining chess with hula hooping, her dad being both a state chess champ and an Ironman triathlete, and her brother Greg adding being great at trivia to his being great at chess. That last one should resonate with many readers, since Greg just became a three-time Jeopardy champ and is an International Master at chess.

I started thinking about my own areas of interest. I am definitely not the most knowledgeable person in the world when it comes to chess, music, 8000-meter peaks, or the wolves of Yellowstone, individually, but combine two of those, and maybe I’m amongst the elite. (Fine, not if you combine chess and music, lol)

Near the end of the book, Jen tells some deeply personal anecdotes about when she and her husband were starting a family, and how their hopes of having multiple children were dashed after a miscarriage. She then talks about how she even learned to apply sideways thinking in situations such as this.

This actually made me reflect back to when my mom became pregnant, not too long after marrying my stepdad. She then miscarried, but eventually, a couple of years later, my brother was born. I wish she were around so I could try to find out if she was able to apply sideways thinking.

I gave a lot of thought to whether to include this last bit in the review. After all, I doubt many people sit down to read a book about learning new ways to apply critical thinking in an effort to improve, and are expecting to read about menstrual cycles and miscarriages. However, there is a larger point to be made here.

Learning to apply new techniques in a never-ending quest for success, such as thinking sideways, is applicable to all aspects of life.

So who is this book for? Well, in my professional life, I manage a team in a commission-based field, so the ability to improve thinking processes can have a strong, direct correlation with the bottom line for those who work on it. I have already bought copies as gifts for other managers at the firm.

I’d say it’s for everyone. Including you.

[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

[Ian Holden · Rating 5 out of 5]

By blending academic research, narrative lived experiences, and introspective exercises, Jennifer Shahade demonstrates the power of thinking sideways.

Drawing from her Grandmaster level expertise in games of strategy, skill, and chance, Shahade is uniquely qualified to mentor those looking to invest their time and energy more wisely. Thinking Sideways equips readers with actionable tools to reframe thoughts, identify patterns, overcome analysis paralysis, and build confidence in risk taking. Additionally, Shahade provides the outlook needed when chance gets the best of us, rather than skill or poor decision making.

Instead of hyper focusing on weaknesses as some coaching methods do, she emphasizes reviewing and embracing our innate strengths to maintain enjoyment and motivation throughout our individual growth.

Ultimately, Thinking Sideways serves as a guide for shifting mindsets to convert strategy into real world success.

[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.

[David MacY · Rating 5 out of 5]

Jennifer Shahade has written an inspiring exploration of a wide range of thinking processes, possibilities, methods, and domains. She combines a warm personal approach with an accessible academically rigorous path in her investigations into this important aspect of humanity. As a champion chess master and poker player, one who was raised by a chess master father and a chemistry professor mother, sharing space with her International Chess Master brother, she has been around deep and complex thinking all her life. Thinking Sideways is a marvelous distillation of her academic studies, personal experiences, professional challenges, and the many varied sources she consulted in preparing this excellent book.
As a chess teacher and former philosophy student who has obsessed over how thinking works, I enthusiastically recommend Thinking Sideways.

[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!

[Aaron Hamlin · Rating 5 out of 5]

This is a fun book that shares problem-solving techniques drawn from the author's personal anecdotes. The author's background in chess and poker makes these anecdotes particularly interesting, often drawing on ideas from game theory. This is a great book if you're looking for an entertaining way to add or polish up tools for your cognitive toolbox. It's a nice bonus that the audiobook is read by the author herself. Worth a listen or read!

[Ashley · Rating 5 out of 5]

This was such a fun read! I loved the chapters on time management and memory. I think she could create a successful workbook or enrichment curriculum based on the material.
There's also lot of interesting chess history that even non players can enjoy. I'm stoked that I got to try out hulachess at the Chess Hall of Fame when I was in St. Louis. Will definitely be gifting this one to others.

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

Good

[John Crippen · Rating 2 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!