I first picked up On the Road while finishing my preparation for the World Under 18 Chess Championship in Szeged, Hungary, in the summer of 1994. Jack Kerouac’s vision was like electricity in my veins. His ability to draw sheer joy from the most mundane experiences opened up the world to me. I felt oppressed by the pressures of my career, but then I’d watch a leaf falling or rain pelting the Hudson River, and I’d be in ecstasies about the raw beauty. I was on fire with a fresh passion for life when I traveled to Hungary.

Over the course of the two-week tournament, I played inspired chess. Entering the final round I was tied for first place with the Russian champion, Peter Svidler. He was an immensely powerful player and is now one of the top Grandmasters in the world, but going into the game I was very confident. He must have felt that, because Svidler offered me a draw after just half an hour of play. All I had to do was shake hands to share the world title—it was unclear who would win on tie-breaks. Shake hands! But in my inimitable leave-it-on-the-field style that has won and lost me many a battle, I declined, pushed for a win, and ended up losing an absolute heartbreaker.

That night I took off across Eastern Europe to visit my girlfriend in a resort village in Slovenia. She was the women’s chess champion of her country, and was about to compete in a major tournament. A rucksack on my back, On the Road in my lap, I took trains and buses and random car rides, digging it all with a wired energy. I ended up in a little town called Ptuj, and will never forget the sight of Kiti walking toward me on a long dirt road, wearing a red sundress that moved with the breeze and seemed out of character, too soft. As she came closer, her head tilted to the side; in her beauty was something severe, distant, and a chill came over me.

Our relationship was a rocky one, and we ended up fighting for two days straight until I left, exasperated, heartbroken, working my way back around war-torn Croatia to Hungary so I could fly home. I finished On the Road in the middle of the Austrian night, sheets of rain pounding down on an old train as it groaned into the darkness, a drunk Russian snoring across the car from me, mixing with the laughs of gypsy children in the compartment next door. My emotional state was bizarre. I had just lost the World Championship and the love of my young life, and I hadn’t slept in six days, but I was more alive than ever before.

Three weeks later, I was standing on a Brazilian street corner the day before representing the U.S. in the World Under 21 Championships, and suddenly Kiti was in front of me, smiling, looking into my eyes. We laughed and our adventures continued. Such was my life.

After finishing On the Road , I began reading The Dharma Bums , Kerouac’s fantastic story centering on the Beat Generation’s relationship to Zen Buddhism. I believe this was my first real exposure to a (albeit rather eccentric) vision of Buddhist thought. I loved the hedonistic internal journeys and rebellious wisdom of Gary Snyder. I yearned to retreat into the mountains and live with the birds. Instead I went to the Shambhala Center in downtown Manhattan and studied meditation. I tried to chill myself out, sitting cross legged on the floor, focusing on my breath. I had moments of peace, but for the most part I was boiling with a hunger to leave everything behind.

That’s when I took off to live in Slovenia, and it was in my European wanderings that I found the Tao Te Ching—an ancient Chinese text of naturalist musings, believed to be written by the hermetic sage Laotse (also known as Lao Tsu) in the 6th century b.c.e. I described earlier how during these years my relationship to chess became increasingly introspective and decreasingly competitive. A large factor in this movement was my deepening connection to Taoist philosophy.

Studying the Tao Te Ching, I felt like I was unearthing everything I sensed but could not yet put into words. I yearned to “blunt my sharpness,” to temper my ambitions and make a movement away from the material. Laotse’s focus was inward, on the underlying essence as opposed to the external manifestations. The Tao Te Ching’s wisdom centers on releasing obstructions to our natural insight, seeing false constructs for what they are and leaving them behind. This made sense to me aesthetically, as I was already involved with my study of numbers to leave numbers . My understanding of learning was about searching for the flow that lay at the heart of, and transcended, the technical. The resonance of these ideas was exciting for me, and turned out to be hugely important later in my life. But for an eighteen-year-old boy, more than anything the Tao Te Ching provided a framework to help me sort out my complicated relationship to material ambition. It helped me figure out what was important apart from what we are told is important.

When I returned to America after my time in Europe, I wanted to learn more about the ideas of ancient China. In October 1998, I walked into William C. C. Chen’s Tai Chi Chuan studio on the recommendation of a family friend. Tai Chi is the meditative and martial embodiment of Taoist philosophy, and William C. C. Chen is one of its greatest living masters. The combination was irresistible.

Exerpt From The Art of Learning By Josh Waitzkin