‘Defeat clarifies so much’: Chess grandmaster Maurice Ashley on the power of losing

As college and high school commencement speakers counsel the next generation, how about this advice? Embrace defeat.

This doesn’t mean playing to lose, but rather, if and when you lose, seek to learn from the experience in hopes of improving in the future. This approach has been adopted by NBA greats past and present, from Kobe Bryant to Giannis Antetokounmpo – as well as by American chess grandmaster Maurice Ashley, who writes about it in his new book, Move by Move: Life Lessons On and Off the Chessboard.

“If you win, you’re sort of supposed to,” Ashley says. “You did things you know … the skills you’ve cultivated over the years. It’s the losses that you really remember – the things you didn’t know.”

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Ashley gave his very first commencement address in April at Western Governors University, hosted by the University of Cincinnati.

“I think it’s great, taking lessons from chess and applying them to your life,” Ashley says. “That kind of wisdom can benefit anyone, definitely young people just about to make their way into the world.”

One chapter of the book has a title that many graduates may not want to hear: “Losing (Because You Will Lose).”

As Ashley explains in the book, losing is an inevitability for even the greatest competitors. What makes a difference is how one reacts. Ashley identifies Bryant and Antetokounmpo, as well as his fellow chess grandmaster Irina Krush, as examples of people who have embraced the opportunity to learn from defeat.

“Sometimes you don’t know what you don’t know,” Ashley says. “Defeat and losing clarify so much, or have the potential to do so. Embrace it. Don’t try to run away from it.”

In the book, Ashley shares other counterintuitive observations while shattering myths about elite chessplayers: They don’t have superhuman memories that allow them to see multiple moves ahead. How could they? Almost 300bn positions are possible after just four opening moves. As for that supposedly irresistible momentum during a game that is going well, it’s actually something to be wary of because it instills false confidence. Even the title of grandmaster itself comes in for scrutiny. Ashley likens it to being an advanced beginner in this 1,500-year-old pursuit.

In 1999, Ashley became chess’s first Black American grandmaster. He is a member of the US Chess Hall of Fame, having been inducted in 2016. He marvels that two of his siblings, both ex-world champions, are in the international halls of fame in their own sports – boxer Alicia Ashley and kickboxer Devon Ashley.

“The three of us unexpectedly came from these very humble beginnings and ended up reaching the height of our professions,” he says, while discussing his early childhood in Jamaica and teenage years in New York City. “We had great examples, great role models. I think the tough background we grew up in very much shaped the people we became, the competitive people we became, the success we found here.”

In Ashley’s case, becoming a grandmaster followed an unsuccessful attempt the previous year. Again, what helped was some outside-the-box advice – this time, from another grandmaster, Alexander Shabalov, in a moment Ashley likens to Karate Kid-style counsel from his own Mr Miyagi.

“In order to get anywhere, accomplish any goal, you have to already be capable of accomplishing this goal,” Ashley says. “You have to put your entire soul into practice – doing the exercise, training every day, eating the right way … It’s the same for every goal, any attainment. You have to be already able to attain the goal before actually trying to do it in reality.”

Asked whether he has ever faced racism in chess, he replies, “I did. I think racism is racism – whatever sport you’re in, things will happen,” including “painful incidents” that he experienced.

However, Ashley adds, “I think one thing chess players understand is checkmate. Once people very quickly realized I was a serious student of the game, they had to buckle down, pull their sleeves up and fight to the bitter end.”

The book emphasizes respect for one’s opponent, although it acknowledges that this is a rare quality in all aspects of society, from chess to politics to daily life. Ashley credits the great Magnus Carlsen as someone who was able to decipher his opponents. He mentions how the Norwegian’s understanding of his rival Ian Nepomniachtchi helped Carlsen win a world-record 136-move showdown during a 2021 world championship match in Dubai.

“Understanding what’s happening inside the heads of others is a superpower that is worth cultivating every single day,” Ashley writes.

In the book, Ashley also delves into formative experiences that came out of adversity in his childhood.

His mother emigrated from Jamaica to the US in 1968, when Ashley was two years old. He and his siblings were cared for by their grandmother, and the family did not reunite in the US for another decade. His parents separated, an event that Ashley later spoke to his parents about individually. Each of those conversations proved painful but helpful. Ashley had become a parent himself when he spoke to his mother about the separation, and he gained a new understanding of sacrificing oneself for a child. He also discovered that childhood games of cards and dominoes with his father had been a good training ground for chess.

The book is also a tribute to New York City as a crucible of chess, especially in the pre-internet era.

“New York is a fantastic place to learn chess,” Ashley says. “There’s a robust park scene,” from Washington Square Park to St Nicholas Park to Fulton Park.

Ashley reminisces over picking up the game as a teenager at Brooklyn Tech, and testing his skills at Prospect Park and City College. He believes chess venues in the city can be compared to New York’s legendary Rucker Park, which helped develop the talents of basketball stars such as Kareem Abdul-Jabbar.

If you’ve noticed a bevy of basketball references, there’s a reason.

“It’s my favorite sport,” says Ashley, who brings a chess player’s vision to the game. “When I watch basketball, I see chess pieces on the basketball floor. All of them have different roles, different strengths and weaknesses.”

The introduction to the book notes that Luka Dončić of the Dallas Mavericks, who is now playing in the NBA finals against the Boston Celtics, hones his basketball skills in part by playing chess for hours on end. (The Celtics’ Jaylen Brown is also a chess enthusiast, and Chess.com promoted a challenge involving both players, timed for the finals.) And Ashley mentions Antetokounmpo’s viral comments from last season’s playoffs on embracing defeat after the then-top-seeded Milwaukee Bucks bowed out in the first round.

“No matter what happens, other people have something to say about whether or not you win,” Ashley says in summarizing Antetokounmpo’s message. “Get up, do the work and push harder so you can be better. Those are fantastic words.”

Reflecting on that video led Ashley to share a few more life lessons: Seek slow but steady progress, and remember the unlikely identity of your biggest opponent.

“One match at a time, one step at a time, incremental growth. Keep getting up every day, be better than yesterday,” he says. “The only person you’re fighting against is really yourself.”

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