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In Episode 237 of Anecdotally Speaking, discover why staying true to your strengths and being selective with what advice you take is key to long-term success.

In this episode of Anecdotally Speaking, Mark shares the story of Josh Waitzkin, a chess prodigy who lost his love for the game after being encouraged to change his natural playing style.

This story highlights the importance of knowing whose advice to take, staying true to your strengths, and recognising when external input may be doing more harm than good.

Mark and Shawn discuss the broader implications of this lesson, from business leadership to personal development, and share insights into how we can navigate the constant influx of advice we receive.

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Tags: Storytelling, Decision-making, Strategy, Change

This story starts at 2:01

Josh Waitzkin was born in New York in 1976 and was a child chess prodigy. He first noticed chess when he was six years old in Washington Square Park, where he saw people playing and got hooked. He started playing regularly and got his first coach at age seven. His coach nicknamed him Tiger because of his naturally aggressive, attacking style, and the name stuck.

Playing in Washington Square Park was a great learning ground. He was up against street hustlers who were always trying to psych him out—yelling, screaming, even blowing smoke in his face. He said if you could maintain your presence of mind there, you could do the Frank Sinatra thing: if you can make it there, you can make it anywhere.

Josh described himself as a naturally aggressive and creative player. His style was to create chaos and then find hidden harmonies. By age 10, he played a notable game where he sacrificed his queen and rook in exchange for checkmate six moves later. At 11, he won the U.S. Junior Chess Championship, and that same year, he played an exhibition match against world champion Garry Kasparov and drew.

By 16, he was an International Master. At this point, people were paying attention. He had coaches, and they started telling him he needed to understand how the really conservative players thought. They encouraged him to study world champions like Karpov and Petrosian—players with a completely different, highly positional style. The thinking was that to succeed, he needed to get inside their heads, to ask, what would Karpov do in this situation?

But Josh later reflected that the more he studied these players, the more mentally confused he became. He started to dial back his natural chaos. He described it as losing his internal compass—his internal sense of direction. And at age 18, he quit playing chess. He had lost his love for it.

Years later, he took up Tai Chi and found that he applied the same approach to it as he had to his original chess. And he absolutely loved it. Within two years, he won national championships. He later wrote a couple of books and contributed a chapter to Tim Ferriss’s Learning from Titans.

Looking back, Josh realised what had happened. The lesson? Be careful who you listen to. Everyone’s going to have an opinion about what you should do, but sometimes, the best thing you can do is stay true to what makes you unique.