Thinking Sideways: How Jen Shahade approaches poker, chess and life

Inside PokerStars talks to PokerStars Team Pro, Jen Shahade

February 24, 2026

Interviews

by David Lynch

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9 Minute Read

In one way, PokerStars Team Pro, Jen Shahade was probably hoping to see much more of London last August than she did. She had arrived in the UK with her family in tow to take part in the PokerStars Women’s Summer Festival at The Clermont, Charing Cross Hotel. In fact, the publisher of her latest book – Thinking Sideways – had their offices just a short walk away. All in all, Jen thought she might get out into the city during the tournament and savour the late summer sights.

It didn’t quite turn out that way. She made it all the way to a showdown with Claire Taylor and then went on to scoop the title and the £22,000 main prize.

After that whirlwind, the three-time National Chess Champion and two-time Global Poker Award winner decided to make up for lost time though: “I did stay a day extra after”, she says, speaking to Inside PokerStars via video call from her home in the US, “and I went to the London Eye with my family. It was a super beautiful day, so I had enough time to enjoy it.”

Taking the time

And that’s something Jen promotes and speaks about quite passionately, both in her book and in person – managing your time to be as present as you possibly can be. Not only is it a top life skill, but a very helpful attribute to have in poker too.

“Yeah, I think a lot of it is, again, going back to being present, and that’s the thing about time management. It is devoting time to the things that you care about and sticking to it,” she says.

“So, you know, one thing that, whether it’s poker or chess study or any kind of devotion, whether it’s writing – if you’re trying to write a novel – quality is so much more important than quantity, in my opinion.”

Jen explains further: “Really thinking and being present and being able to give all your attention to something, even if it’s not that much time, in terms of the minutes and the hours, it can be so unbelievably valuable.”

Keeping Focused

With her new book out this month, the author and commentator is rarely not busy. She has won poker tournaments across the globe, from London to Prague to Las Vegas, and that’s even before getting to her hugely successful chess career. Her mind must be constantly going. How does she keep focused, both at the tables and in everyday life?

Jen reveals her poker approach.

“In my recent success in Las Vegas, where I got third place in the North American Poker Tour, which was my biggest cash, I used a little notebook, which is just the size of a phone, a tiny, little notebook. I put it in my little cup holder, and I would sometimes scribble a little note about a hand. Of course, not when I was playing, you know, on a break or something, or when the dealer was moving, and I felt that that was really useful because I didn’t get out my phone, but I was also able to just stay present by kind of releasing the past.”

She continues: “But the studies that show the importance of handwriting often bear out that part. It’s partly the tactile, but it’s also partly that it’s slow. That’s good that it’s slow, because then you’re given more time in those breaks to think and remember.”

The PokerStars Team Pro says it surprised her how much of a difference it made to her game.

“I think the thing about the phone is we all hear these demonizing stories about the phone, but even if you were to put the phone in airplane mode, it still has so many associations, because there’s just so much going on there. It’s like a million connections, it’s like the whole world at your fingertips, which is obviously, very convenient in many ways, and has changed our lives in so many, good and bad ways, but, when you’re playing, like, a poker tournament, you don’t need all that. You kind of want to be present. Again, it’s all about being present.”

Chess and Poker

Having had great success in both chess and poker, she has a unique perspective on the similarities between both games.

“I think that the biggest similarity [in both poker and chess] is the approach to studying the game. Trying to kind of look for the things that come up again and again. And many of us who play either chess or poker are not doing it full-time, so it’s not like Magnus Carlson studying 6 hours a day, or, you know, super high rollers studying 8 hours a day when they’re not.

“So, it’s key to think about the situations that will come up most often, and try to prepare for them, and that type of mentality comes up very much in chess and in poker. Like, the stack size you might get the most often, the position you might get the most often, the flop you get the most often. Same thing in chess, you know, there are even databases that show you what people play in the opening at different levels.”

The chess Olympic medalist continues: “And so, sometimes there’s a move that they play 80% of the time. And, of course, then you want to study that, right? And it sounds so obvious, but actually, a lot of times, people just go into a rabbit hole of something that they’re interested in that almost never happens, and that’s, like, part of the title and the point of my book, Thinking Sideways, that we sometimes just get stuck in these rabbit holes without looking at the big picture, what’s likely to happen.

“They’re both mind sports, and they both require a lot of travel, especially if you’re playing the live circuit, but even if you’re playing online, it still is physically rigorous and so you definitely need to really plan your routine with the idea that you’re an athlete. So, prioritizing your sleep, and nutrition and just tracking your energy.”

What about the differences between the two games?

“The difference is that in poker you lose a lot, and it’s a game of winning big, more than it is winning often”, explains Jen.

“So, you know, if you can win a big pot, that’s worth more than winning two smaller pots, and this is extremely difficult psychologically. I think it’s one of the hardest things for new players or amateur players to grasp.

“Whereas players who haven’t accustomed themselves to that yet are still after just, like, any kind of win, because any kind of win feels good. And so, it’s weird to have to psychologically circumvent that. Now, in chess, we don’t really have to deal with that, because, you know, it’s a binary game.”

Reframing Regret

Some poker players can get caught in the infinite loop of looking back at the bad plays or losses with abject regret. It’s an almost instinctive human trait. However, in her new book Jen uses a phrase which is interesting – ‘regrets inspire you’: what does she mean by that?

“I think that it’s just regrets often show that you were thinking about different options”, she offers. “That’s what I meant in that part. It’s like, when you’re thinking sideways, you’re always going to be thinking a lot of different options, so it would be literally impossible to never choose the one that you later think was not the best.

“Just like in poker, and I think chess as well, if somebody finishes the day and says that they have absolutely no regrets and they played perfectly, I mean, of course, if they’re saying it like, ‘I want to move on to the next day’, that’s a great mindset to have, but if they mean it literally, and it’s No Limit Hold ‘Em you know, it’s a bit strange, because there’s so many different bet sizes. Probably there’s, like, some kind of regret, you know? There’s always something you could have done a little better. I think it’s being honest with yourself and still being able to be positive is a real great skill to have.”

Women’s Poker

Our conversation circles back to London in August 2025 at the PokerStars Women’s Summer Festival, Jen enthuses about the “positive vibe” she felt throughout the event.

“I think it’s amazing. I love the idea of this women’s festival, because so many women, meet and become friends, and it’s just got such a positive vibe. I think a lot of times it’s that strong leadership that really sets the vibe, and, you know, KJ (Kerryjane Craigie, fellow PokerStars Team Pro) at the Hippodrome is always so fun, but then also so respectful of the game.

“She really cares about putting on the events in a way that allows the women to showcase their skills while also having fun, and you really feel that vibe throughout. And one thing that I love about the festival, even though I know that some players might get nervous about this, I love that there’s TV commentary of the final table, and there’s a featured table.

“It’s just so good for women who are also playing in mixed fields, potentially even bigger buy-ins, and they get to practice having their whole cards revealed and still playing their ‘A’ game, you know, that’s not easy. And the fact that you get to practice in a 400-pound event I think is super, valuable.

“And, you know, if you have a coach, you can have them go over it and see if you’re giving off any tells. It’s incredibly valuable. You would potentially have to pay so much money to have that done if you didn’t get a chance to do it yourself.”

Thinking Sideways

How Jen found the time to write a book is anyone’s guess. But her mental application to both poker and chess, and life admin, seems solid and working for her. What was it that made her want to write Thinking Sideways: How to Think Like a Chess Player and Win at Life?

“I’ve always wanted to write a book like this, where I talk about chess and poker and applications to real-life thinking because I’m obsessed with thinking about thinking, I think I’m thinking, like, all the time, which maybe a bit too much, but because of that, I feel like there’s so much I have to share with other people about how we can think differently, how we can think in a way that allows us to see opportunities that others don’t.

“Because that’s really the whole concept of thinking sideways, and what can make you better at chess or poker or life, even if you can’t devote the same number of hours.

“So really, it’s honestly to help people and to entertain people, even if they don’t become super serious gamers themselves and I’ve always dreamed of writing a book like that, because I love reading books like that myself.”

Adding: “I found it to be extremely challenging, so it took me longer than most books, but I’m happy with the final result.”