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“Identify the strengths within so you can become the champion of being you.” —Jennifer Shahade
Chess. At first, the idea of thinking like a chess champion may sound like an impossible feat if we do not know how to play the game, but as winner of two U.S. Women’s Chess Championships and the first woman to win the U.S. Junior Chess Open, Jennifer Shahade shares in her new book, it all comes down to thinking well. Or to put it more precisely, thinking sideways.
In my conversation with Jennifer, who is also a two-time Global Poker Award winner and silver Olympic medalist, she will share what she means by her chosen title, and then we will dive into specific decision-making strategies that champion chess players like herself use and how they also translate into creating a life we love living.

Thinking Sideways by Jennifer Shahade
Released April 7, 2026
As I share in the episode, and long-time readers of TSLL will remember that chess has always been a game I have wanted to learn. So it was both my love of critical thinking strategies as well as my curiosity about the game of chess that led me to Shahade’s book – Thinking Sideways that was released in April. And of course, I had to ask her what she recommends for how to get started as a beginner to the game. Her advice, while she did suggest reading various books on chess (view all of her books here, even though not geared toward the beginner, are definitely perfect for the seasoned player) – not one title in particular, is actually YouTube videos paired with visiting Chess.com. And so I did some searching around and found this video that I think would be an ideal Beginner’s video to keep in your library (it is what I will be doing in the coming months, slowly, but surely).
Be sure to tune in to the audio version of our conversation as we will talk about the power of embracing intermezzos, why presence is crucial to seeing and then seizing opportunity, why focusing on our strengths is far more valuable than zeroing in on our weaknesses and many more worthwhile pieces of life advice as witnessed through the lens of the game of chess. I do hope you enjoy the episode as Jennifer was a great guest and shared freely. And her Petit Plaisir offers a new perspective on a word we may have unfairly defined negatively.
Purchase
Thinking Sideways: How to Think Like a Chess Player and Win at Life
by Jennifer Shahade

Find and learn more about Jennifer Shahade:
- View her website – jennifershahade.com
- Check out her substack – jenshahade.substack.com
- Instagram: @jenshahade
- Poker fans, listen to her award-winning podcast The Grid
- Explore all of Jennifer’s books, many focused specifically how to play chess.
Explore more episodes of The Simple Sophisticate here
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