From the age of six when he first discovered chess, Josh Waitzkin has lived a life of constant learning and tenacious pursuit of Quality. Now Josh uses the lessons of his training to guide elite performers of business, athletics, and social impact on their own journeys to self expression.

By exploring themselves more deeply, and unearthing and internalizing nonlocal principles that connect their arts to others, elite performers and artists transform their journeys to virtuosity by amplifying what makes them unique (what Josh calls their “funk”), generating their own training ecosystems, and harnessing the power of thematic interconnectedness.

Josh’s approach generates a way of life that helps performers understand their conceptual schemes, evaluate the underlying assumptions and dependencies, and embrace their dynamic flux. By releasing static patterns, performers can make astonishing creative leaps, while the technical foundation becomes intuitive and visceral.

These ways of living and training were born in various arenas of competition—both mental and physical—and have been proven in sweat and blood, not words. Josh’s journey through seemingly disparate arts helped him cultivate these principles and continues to give life to new ones. 

EARLY CAREER: CHESS

Josh’s journey into the art of training began with chess. With intensive study and competition, Josh transformed the technical into the intuitive. Later, in his book, The Art of Learning, Josh would call this concept Numbers to Leave Numbers, or Form to Leave Form. It’s rooted in an ingrained knowledge of Dynamic Quality, as (un)defined by the philosopher Robert Pirsig.

“I have a beacon for Quality that I cultivated through chess,” he said in the afterword of the new edition of Searching for Bobby Fischer. “If you cultivate a beacon of Quality—if you know what Quality feels like—you can follow it like a map.”

Dynamic Quality began to emerge in Josh’s chess game at age seven, stemming from formal training under Bruce Pandolfini, and the hardscrabble lessons of the street hustlers and virtuosos of Washington Square Park. Josh combined both to form his aggressive, intuitive style of play.

From age nine on Josh dominated the U.S. scholastic chess scene, becoming an eight-time National Champion. He won the National Primary Championship in 1986, the National Junior High Championship in 1988 while in the fifth grade, and the National Elementary Championship in 1989. At the age of 11, he drew a game with World Champion Garry Kasparov in a simultaneous exhibition. At age 13, Josh earned the title of National Master. He won the National Junior High Championship for the second time in 1990, and the Senior High Championship in 1991, as well as the U.S. Cadet Championship (Under-16). Between the third and ninth grades, Josh also led New York City's Dalton School to win six National team championships.

In 1993, Paramount Pictures released the film Searching for Bobby Fischer, based on the highly acclaimed book of the same title written by Fred Waitzkin, documenting Josh's journey to winning his first National Championship. That same year, at 16, Josh became an International Master and the U.S. Junior (Under-21) Co-Champion. In 1994 he won the U.S. Junior Championship and placed fourth in the Under-18 World Championship.

Tai Chi Chuan and The Art of Learning

Then Josh moved on. 

“I think that my ability to succeed at different disciplines has had to do with turning the chapter,” he said in the afterword of Searching for Bobby Fischer. “I do it decisively and rarely look back.”

Though he left chess and began his martial arts journey, the lessons absorbed from years of training endured and evolved. One, Parallel Learning, fueled his explosive growth as a fighter. The idea behind Parallel Learning is that a student can experience a transition of level from seemingly two disparate arts or pursuits by leveraging the principles and embodiment of Quality of one art into the other.

“When I won my first Push Hands National Championship I was only two years into the martial arts and I realized something special had happened inside me,” Josh said. “Around this time I was playing a 40 board simultaneous chess exhibition to fund muscular dystrophy research. I had this experience an hour into the simul that I was feeling flow and filling space left behind. I wasn’t playing chess exactly. I was riding the energetic wave of the game. It felt like I was playing tai chi push hands rather than chess. I realized that the barrier between these two arts had been broken down. And inside of me they were the same. I had taken the essence of one thing and applied it to another.”

Josh’s training of Tai Chi Chuan began at 21 under the Grandmaster William CC Chen. He was drawn into the art by his love for eastern philosophy and meditation, and by the desire to begin a learning process anew, as a total beginner, away from the spotlight that constantly followed his chess career. In Chen, Josh found the teacher that he had always searched for, “a great master with the humility and generosity that true Quality is all about.”

Initially Josh had no intention of competing in the martial arts, but there was no stopping the inevitable. For five years straight Josh was the Tai Chi Chuan Push Hands Middleweight National Champion in the Restricted Step and Moving Step divisions. In December of 2002, Josh won the Bronze Medal in the Push Hands World Championship in Taiwan. In early November of 2003, Josh won the Gold Medal in the Push Hands division of the World Kuoshu Championships in San Paolo, Brazil. In July of 2004, Josh competed in multiple weight divisions at the National Championships in Orlando, Florida. He won an unprecedented total of five National Championship titles in the Middleweight, Light Heavyweight, and Heavyweight divisions. 

Josh’s competitive Tai Chi life came to a dramatic climax at the seventh Chung Hwa Cup International Tai Chi Chuan Championships in Taiwan December 4-5, 2004, where he worked through a brutal field and won the Middleweight World Championship title in Fixed Step Push Hands and became the Middleweight World Co-Champion in Moving Step Push Hands.

In 2007, Josh would distill the knowledge and experience gleaned from his chess and Tai Chi Chuan training into The Art of Learning: An Inner Journey to Optimal Performance. The book also launched his peak performance consulting career. In 2008, Waitzkin founded The JW Foundation, an educational non-profit dedicated to an individualized approach to learning.

Jiu Jitsu

A confluence of factors brought Josh to Brazilian Jiu Jitsu. The first was breaking an opponent's elbow in the climactic moments of his final Tai Chi Chuan tournament (this match is described in the last chapter of The Art of Learning). The amorality of the act left its mark on Josh and the damage he inflicted was something he was reluctant to repeat. He decided to become a beginner again. 

As Josh's standup practice grew more sophisticated, the natural evolution of fight sports brought him to the ground. He began training Brazilian Jiu Jitsu (BJJ), a grappling art that focuses on subduing and controlling adversaries through positional dominance, joint locks, and choke holds. Jiu Jitsu, often translated as “the gentle art,” lacks the ballistic impact of striking. BJJ allowed Josh to deepen his relationship to Dynamic Quality through the energetic dance of this emergent and devastatingly effective sport. 

Josh began cross-training in BJJ in 2002, but his primary martial art was still Tai Chi Chuan. Then after winning the 2004 Push Hands Worlds, he moved to Los Angeles for a year in early 2005, wrote The Art of Learning (after five years of taking notes and brainstorming the book), and went all-in on training under legendary BJJ black belt John Machado. When life brought him back to New York City, he trained under Marcos Santos and Marcelo Garcia, who then was splitting his time between New York and Florida. Meanwhile, Marcelo was igniting the Jiu Jitsu world with commanding ADCC and IBJJF world championship wins.

Marcelo’s dynamism and innate sense of Quality were powerful attractors. As a competitor, Marcelo constantly refined, then reinvented his game. On the mats, he consistently sought the most challenging training partners and the exposure that they might bring, knowing that ultimately exposure strengthened his game. And perhaps most strikingly, Marcelo had a sense of abundance and willingness to share his techniques. This was rooted in generosity and a deep-seated conviction in the inevitability of success—that no competitor could ever know or execute Marcelo’s game better than Marcelo.  

“Marcelo Garcia is maybe the greatest transitional player in the history of Jiu Jitsu,” Josh said on Episode 148 of the Tim Ferriss Show. “The essence of his game is to not hold, to allow people to move, and to embrace the chaos and get there first. He has cultivated the transitions so systematically that he has 10 frames in transitions where somebody else will just be moving from one position to the next. But that transition, itself, is his ocean. It's a beautiful thing to see.”

Josh wanted to bring Marcelo’s game and learning approach to a global audience with what would become MG In Action, a first-of-its-kind digital platform for studying Jiu Jitsu that enhanced learning through the interconnectedness of theory and practice. But Josh told Marcelo that they could only pull it off if Marcelo relocated to New York City.

They opened the New York City school in 2009. The academy would be a pressure cooker for top grappling talent and give life to MG In Action, which would become a virtual laboratory for training the technical and conceptual aspects of Jiu Jitsu as well as the principles of The Art of Learning.

As the school took root, Josh was training and competing with the intention of eventually making a run at ADCC, the Super Bowl of submission grappling. His days consisted of grueling double sessions that left little time or energy for much beyond life’s basics. 

A training mishap brought the Jiu Jitsu journey to an abrupt halt. He was a brown belt and expectant father when he broke his back during a live sparring session. The injury was so severe that he couldn’t lift his newborn son for many months.  

The physical pain and emotional turmoil were excruciating. Both forced a reckoning.

As Josh healed over the next year, he remained committed to his dreams in BJJ, and incrementally amped up his training (perhaps more than he should have). He became Garcia’s first black belt in 2011, and resumed an intensive training rhythm despite having never made a full recovery from his injury. 

He loved the art more than ever, and was playing a higher level game on the mats than he ever had … but other times he could not walk. Then came the fateful moment a group of top sports doctors showed him his MRI and told him if he kept training BJJ he would be crippled for life.

He knew it was true. He had to move on. This time, against his will. 

The next years of Josh’s life were soulful, searching, and restless. He tried to love training others with the same intensity that he had always loved training himself. He poured himself into his peak performance consulting work and began to explore new arts, searching for something that suited the dynamism of his learning style.

Foiling

Fatherhood shifted something in Josh, navigating him toward nurturing and away from fighting. In many ways, this shift brought him back to where it all began: the water. Fight sports had been about managing and manipulating other bodies and minds. But the call back to the water was in many ways about surrendering to and receiving the ocean’s power.

As a young boy, Josh’s intense stretches of chessic competition were punctuated by summers at sea aboard an old family fishing boat, the Ebb Tide, trolling for blue marlin, spearfishing for meals in sharky waters, and navigating the perils of open ocean life as a family while anchoring out for weeks at a time between Bahamian islands.

Away from Bruce Pandolfini, his first chess instructor, the water served as Josh’s teacher. He learned to be at peace in intense storms, at ease in its depths spearfishing and freediving surrounded by predators, and intently focused reading the signs of the ocean in pursuit of large gamefish.

In some ways, transitioning from Jiu Jitsu to watersports was like a homecoming. He was a beginner again, but simultaneously immersed in the dynamic wave energy that he’d ridden through his other pursuits. Except this time, where Jiu Jitsu attempts to contain that energy, foiling harnesses it.

“I’ve never been more in love with an art in my life,” Josh said on Episode 412 of the Tim Ferriss Show. “I think that so much of how I relate to foiling is its frictionlessness. I think of learning as unobstructed self-expression. Friction is a form of obstruction. What’s fascinating is that foiling is such a powerful physical embodiment of that principle.”

Unlike conventional surfboards, foiling uses hydrofoils—submerged wings that glide below the water’s surface and attach to the board with a mast. The technology offers many advantages. One is speed. With no surface contact between the water and the board, the rider harnesses hydrodynamics to achieve speeds that far outpace conventional boards.

Another advantage is ride time and maneuverability. The rider can pump the wing (a subtle process that involves driving the wing down into the water column and then deweighting to allow it to rise back up to the top of the mast) to power through stretches of flat water between waves, and ultimately to connect multiple waves. This freedom of movement translates to more time-on-wave and learning opportunities. While surf culture tends to have a scarcity mindset, foiling is abundant. There is no need to compete for the exact same wave. The entire ocean becomes a playful training ground. 

As with other disciplines, Josh began his pursuit of foiling by deconstructing it to the component parts, then training the technical and thematic aspects of those components. To train the flight dynamics of foiling, Josh logged thousands of miles on flatwater, using an eFoil, a battery-powered foil board. Simultaneously, he trained breakfalling—a core component of the martial arts – that turns an unplanned fall into a controlled fall, or a fall that proactively integrates certain core dynamics that soften the impact–and thus liberates the artist from both a fear of falling and its potentially devastating implications. This is particularly critical in foiling where the guillotine-like mast and sharp wing can be catastrophic if they make impact with the foiler during a fall. When away from the water, he rode a Onewheel, a powered skateboard with a single wheel, to train the balance and turn dynamics, and more breakfalling. 

“When you learn a technique, you’re learning one thing. When you learn a principle that embodies a technique, you might be learning a thousand things. And when you internalize a principle that crosses the boundaries between arts, you are learning about life itself,” Josh said. “I design learning processes around the meta. This is part of the reason why I think my approach to surfing and foiling has looked so strange to lifetime surfers because I’m not approaching it locally. I’m working on internalizing certain core concepts, universal principles, and I’m integrating the technical landscape in that context.”

Inspired by surfing great Laird Hamilton after spending a week together in Kauai and watching Laird foil, Josh began experimenting with tow-in foiling: Using a jet ski to drop a tiny 3.5 foot, 4 pound tow foil board into massive offshore breaks that are traditionally out of reach without the aid of external power. For Josh, this is the dynamic edge of foiling. Once in a wave, the minimalistic equipment and artist become one. 

There is no swing weight or inertia. It is pure receptivity. These training sessions are some of his most intense. The wild speeds, incredible precision needed to manage and maneuver the smallest and fastest foil wings while hunting the apex of powerful long period Pacific waves, and the relentless proximity to annihilation stretch the mind to its absolute limit.  

Of course, the ocean tries to find creative ways of killing you. In Josh’s case, there has been a crocodile that had an uncanny resemblance to a floating tree, three stingrays that skewered his legs, and countless uproarious falls at upward of 40 miles per hour followed by washing machine hold downs where the ocean pins and tumbles him deep until she is ready to release her grip.  

But, this is home for Josh. It’s a space that few would inhabit by choice. But those who do stand the chance of discovering the catalytic place where brilliance dances with blunder, and the wave energy of possibility is strongest.