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The Distillery · Volume V

The Distillation of Josh Waitzkin

The Path to Mastery

National Chess Champion at 9. Tai Chi World Champion. Brazilian Jiu Jitsu black belt. How was he able to reach the pinnacle of three disciplines that on the surface seem so different? This distillation uncovers the themes and principles that have guided Josh’s journey on the path to excellence.

Key Themes

Unobstructed Self Expression

Thematic Learning
Depth over Breadth
Go towards Stress & Tension
Life Works in Oscillation
Something that has always fascinated me is the concept of a Polymath or Renaissance Man — a person who has many talents and knowledge in multiple domains. One of the modern day polymaths I’ve learned the most from is Josh Waitzkin. When it comes to touching excellence in multiple domains Josh is one of the best. Waitzkin was a National Chess Champion at the age of 9 and then took on the martial art Tai Chi Chuan and ultimately earned the title of World Champion. He since then has become a Brazilian Jiu Jitsu black belt.
This distillation will be uncovering the themes and principles that have guided Josh’s journey on the path to excellence in multiple domains. Josh is someone who is in search of wisdom, foundational principles and a better way of going through life. It’s a search, a journey that never ends and one we’re all on. Waitzkin doesn’t sit back and theorize about life, he goes all in. His knowledge and understanding is based on action not philosophizing. For Josh his real journey has always been the inner journey.
“When I think of Josh Waitzkin, I think of vitality. Love has driven his supernormal learning and achievements. When I seek words that best point to his character and values — passion, joy, introspection, intuition, integrity, authenticity, creativity, self-expression, and unlearning come to mind.”
Those who succeed at the elite levels of any discipline have built relationships to learning around subtle introspective sensitivity. They understand how their minds work, and both cultivate strengths and take on weaknesses through their unique natural voice. They have learned to open communication between their conscious and unconscious minds, and construct repertoires around moments of creative inspiration. They have built triggers for their peak performance state, learned how to funnel emotion into deep focus, turned adversity to their advantage as a way of life — and they have done all of this in a manner and language that feels natural to them. That is how they seem so unobstructed, so fluid… they are just being themselves. Like children.
In my experience, successful people shoot for the stars, put their hearts on the line in every battle, and ultimately discover that the lessons learned from the pursuit of excellence mean much more than the immediate trophies and glory. In the long run, painful losses may prove much more valuable than wins — those who are armed with a healthy attitude and are able to draw wisdom from every experience, “good” or “bad,” are the ones who make it down the road.

01

Unobstructed Self Expression

“Everything I’ve done when I’ve been flying in my learning process, in my performance, psychology and my competitive energy, it’s been a form of self expression, love, and when I’ve been obstructed, it’s been trying to fit into a mold that wasn’t right for me.”
To be truly elite you have to express who you are at the core through your art. I believe that one of the most critical factors in the transition to becoming a conscious high performer is the degree to which your relationship to your pursuit stays in harmony with your unique disposition. Josh has trained himself to be true to himself because that’s when he works best. He has an allergy to doing anything else.
There will inevitably be times when we need to try new ideas, release our current knowledge to take in new information — but it is critical to integrate this new information in a manner that does not violate who we are. By taking away our natural voice, we leave ourselves without a center of gravity to balance us as we navigate the countless obstacles along our way.
Ultimately you have to embrace your funk; embrace your eccentricity; embrace what makes you different and then build on it.
“I have built a lifestyle around being true to myself. Maybe a big reason is because my mom used to always tell me as a kid to follow my heart, follow my dreams. I never made decisions for money or for external things. I always trusted that if I was true to myself, these things would follow.

02

Living on the Other Side of Pain

“I’ve trained for many, many years at this principle of living on either side of pain: learning to turn what feels uncomfortable, learning to turn that place of mental resistance at the stretch point into something that I crave, that I love, that I enjoy.”
To achieve excellence, a counterintuitive notion: most people seek to avoid pain and discomfort. After you achieve some mastery, you learn to ignore the pain. You must seek it out and embrace it.
Most people avoid the stretch points in life, so they’re mediocre. But it gives us opportunity — if we live at our stretch point, there will be pain. We can change our relationship to discomfort so we hunger for the growth edge rather than hide from it. You have to fully engage. But also have an understanding that disappointments provide the greatest insights.
“First you feel pain, the panic ‘get me out of here!’ But you must come to peace with that pain and learn to enjoy it. It’s learning to completely love chaos till the tension isn’t grinding on you. You’re not a tectonic plate moving toward eruption, you’re getting stronger as the tension builds.”
If you want to be a world-class performer, mental resilience is arguably the most critical trait. The moment we believe that success is determined by an ingrained level of ability as opposed to resilience and hard work, we will be brittle in the face of adversity.
“The setbacks taught me how to succeed. And what kept me on my path was a love for learning.”

03

Depth Over Breadth

“My approach is one that prioritizes depth before breadth. Almost everyone goes the other way, breadth first or go wide and then deep. Or maybe go wide and never go deep, which is actually what our culture tends to be moving toward — everyone’s distracted doing a million things at once.”
The theme is depth over breadth. The learning principle is to plunge into the detailed mystery of the micro in order to understand what makes the macro tick. This has the potential to distinguish success from failure in the pursuit of excellence.
In our world today everyone races to learn more and more, but nothing is done deeply. Things look pretty but they are superficial, without a sound body mechanic or principled foundation. Nothing is learned at a high level and what results are performers who are operating on a suspect foundation.
“If you do something with incredible depth, you develop this feel for quality. That’s what I want for my kids. I want them to explore quality and love and have them just feel how beautiful it is to do art deeply in a way that they are so passionate about.”
Let’s say we have three skills to learn. The typical approach is to take them all on at once. It is much more effective to plunge deeply into one, touch Quality, and then transfer that feeling of Quality over to the others. This approach engages the unconscious, creative aspects of our minds, and we start making thematic connections which greatly accelerate growth.
Depth beats breadth any day of the week, because it opens a channel for the intangible, unconscious, creative components of our hidden potential.

04

The Principle of Quality

“It’s such a beautiful, incredible principle. Most people think they can wait around for the big moments to turn it on. But if you don’t cultivate turning it on as a way of life in the little moments — and there’s hundreds more times little moments than big — then there’s no chance in the big moments.”
Josh learned the principle of quality from Robert Pirsig’s book Zen and The Art of Motorcycle Maintenance. Quality for Waitzkin is both a process and an outcome. It is the process of learning to do something exceedingly well, or learning an exceedingly good way to do something. And it is the result that one savors or relishes.
Once you’ve tasted quality in one element of your life you are always in search of it. The little things are the big things because they’re a reflection of how you do anything is how you do everything.

05

Making Smaller Circles

“Turning the large into the small. Touch the essence of a technique, and then incrementally condense the external manifestation of the technique while keeping true to its essence. Over time expansiveness decreases while potency increases.”
A classic example of this is Bruce Lee and his famous One Inch Punch. Lee reached a level of quality where his punch packs so much potency even from one inch where others may take a foot to develop the same type of power.
If I understand a series of movements more deeply, in more frames, with more detail, then I can manipulate my opponent’s intention without him realizing what happened.

06

Thematic Interconnectedness

“Lateral thinking or thematic thinking — the ability to take a lesson from one thing and transfer it over — I think is one of the most important disciplines that any of us can cultivate.”
One of Josh’s greatest strengths as a learner is his ability of Parallel Learning or Lateralization. He’s been able to understand the foundational building blocks across different domains and translate them from one another. This is how he’s gone from a world class chess champion to a world class martial artist.
When you learn a technique, you’re learning one thing. When you’re learning a principle that embodies a technique, you might be learning a thousand things. Design a learning process around the meta. Internalize core concepts, principles. The techniques fall within the tree beneath the principle.

07

The Internal Spirit — Your Teacher 20 Years From Now

“No one will know me better than myself 20 years from now. If my goal is unobstructed self-expression, then the person who’s teaching me should be the person who knows me most deeply. And that’s my person 20 years from now.”
This visualization is designed to help you know what you don’t know.
“It’s so easy to think that we were in the dark yesterday but we’re in the light today, but we’re in the dark today, too.” Avoid people who claim to not be in “the dark” — they don’t understand themselves enough if they claim that.

08

Finding a Teacher

The key to finding a teacher is finding someone who can truly understand us. The vast majority of teachers teach the way they learn. They have their way and teach all their students that way. By definition it will alienate 75% of the students. So find the teacher that listens first.
“When I train people, 99% of what I do is listening. Not just with dialogue, but study them, through my observation of them, reading their journals, their biometrics. I just try to feel someone deeply.”
We need to find a teacher who will help us on that road to self-discovery. An ideal relationship between mentor and apprentice is a shared love for the art of what they’re doing together.
Feedback is critical but receiving the right feedback is more important than no feedback. Cultivating a close ecosystem of people who you can trust to be honest with you in their pushback is really important.

09

Intuition

“In my opinion, intuition is our most valuable compass in this world. It is the bridge between the unconscious and the conscious mind, and it is hugely important.”
Nearly all of Josh’s revelatory moments emerged from the unconscious. His numbers-to-leave-numbers approach to chess study was his way of having a working relationship with the unconscious parts of his mind. He would take in vast amounts of technical information that his brain somehow put together into bursts of insight that felt more like music or wind than mathematical combinations.

10

The Soft Zone

“I realized that in top-rank competition I couldn’t count on the world being silent, so my only option was to become at peace with the noise. Mental resilience is arguably the most critical trait of a world-class performer.”
Envision the Zone as your performance state. If you are tense, with your fingers jammed in your ears and your whole body straining to fight off distraction, then you are in a Hard Zone that demands a cooperative world for you to function. Like a dry twig, you are brittle, ready to snap under pressure. The alternative is to be quietly, intensely focused — you flow with whatever comes, integrating every ripple of life into your creative moment. This Soft Zone is resilient, like a flexible blade of grass that can move with and survive hurricane-force winds.
A man wants to walk across the land, but the earth is covered with thorns. He has two options — one is to pave his road, to tame all of nature into compliance. The other is to make sandals. Making sandals is the internal solution. Like the Soft Zone, it does not base success on a submissive world.

11

The Learning Phases

Josh approaches learning through 4 stages:
1. Unconscious incompetence — “I don’t know how bad I am”
2. Conscious incompetence — “This sucks. I know how bad I am” (most people quit here)
3. Conscious competence — “I can do this if I focus”
4. Unconscious competence — “I don’t remember the last 10 minutes of driving”
Why do most people quit at Conscious Incompetence? They don’t do the work to truly understand deeply enough. It’s an embarrassing stage if your ego is tied up with it — so suspending the ego is a critical component to getting past it.

12

Focus & Presence

If deep, fluid presence becomes second nature, then life, art, and learning take on a richness that will continually surprise and delight. The secret is that everything is always on the line. The more present we are at practice, the more present we will be in competition, in the boardroom, at the big stage. Presence must be like breathing.
Stress and recovery should be our rhythms. One of many problems with multi-tasking is that the frenetic skipping leaves little room for relaxation, and thus our reservoir for energetic presence is constantly depleted.
Intense Visualization
Your brain has trouble knowing the difference between actually lived experience and an intense visualization experience. This is an incredible superpower for rewiring our brain and it’s a muscle we can develop.
Josh wanted to compete in the Nationals with a broken arm. He resolved not to atrophy through intense visualization practice — doing daily resistance workouts on his left side and after every set, visualizing the workout passing to the muscles on the right. When the cast came off, he had hardly atrophied at all. Four days before the Nationals the doctor cleared him. He won the Nationals.

13

Being at Peace in Chaos

“We ultimately don’t want to be meditating in a flower garden. We want to be able to meditate and have a meditative state throughout our lives — in a hurricane, in a thunderstorm, when sharks are attacking you — any moment.”
Three critical steps in a resilient performer’s evolving relationship to chaos:

14

Life Works in Oscillation

“Most people in high-stress, decision-making industries are always operating at this kind of simmering six, as opposed to the undulation between deep relaxation and being at a 10.”
In order to switch on intensely you need to switch off intensely. In order to focus 10/10 you need to relax at 0/10. Build in rest and recovery for all elements of life.
In virtually every discipline, one of the most telling features of a dominant performer is the routine use of recovery periods. Players who are able to relax in brief moments of inactivity are almost always the ones who end up coming through when the game is on the line.
Because waiting is not waiting, it is life. I believe an appreciation for simplicity, the everyday — the ability to dive deeply into the banal and discover life’s hidden richness — is where success, let alone happiness, emerges.

15

Creating Performance Triggers

A physiological connection is formed between the routine and the activity it precedes. Once the routine is internalized, it can be used before any activity and a similar state of mind will emerge. Gradually and incrementally condense the routine — in short order, you will be able to produce all its benefits by merely thinking about it.

16

Growth Mindset & Plateaus

Growth comes at the point of resistance. We learn by pushing ourselves and finding what really lies at the outer reaches of our abilities. You would praise a kid for the process versus the outcome — “I’m so proud of how hard you worked” not “You’re so smart.” Focus on the process and not the outcome.
Plateaus are where most people drop off. They’re long and arduous and the mental resilience to push through when little to no progress is being seen is essential. Learn to love the plateaus.

17

The Most Important Question

The “Most Important Question” is a journaling routine where each working day you end with thinking: “What’s the most important question in what I’m doing right now?” Pose the question to the unconscious and then wake up first thing in the morning and brainstorm on it.
After a month, look back at your journals and think: “In the moment, this is what I thought was most potent but now I realize this would have been most potent. What’s the gap?” Deconstruct the gap and design your training process around it. You’re training yourself, day in and day out, like water, to be an increasingly potent thinker.

18

What Almost Dying Can Teach You About Living

Josh almost drowned in a New York City pool after doing long breath holds during his swim workout. He was unconscious at the bottom of the pool for 4 minutes before someone pulled him out. The doctors said he would have been brain dead if not for his training.
“After that I just decided that I would devote my life to living as fully and deeply and beautifully as I possibly can, helping my loved ones live as fully and deeply and beautifully as they could and making as large and positive an impact on the world as I could.”

If you were going to die in two years in perfect health, left undone what would you most regret not doing? What will you do in the next two years?

✦ ✦ ✦

19

Josh Waitzkin's 20 Principles of Learning

These principles form the foundation of Josh’s approach to mastery across every domain he’s entered.
1. Resilience
Value process before results. True learning occurs through a process of hard and sustained effort. It is more important to draw insights from every step we take rather than focus on any end reward or goal. Labels like “winner,” “loser,” “smart” or “dumb” should be avoided — they lock our sense of ourselves in place.
2. Investment in Loss
We expand our minds by allowing ourselves to confront hurdles, experience losses, and take a good hard look at them. A willingness to lose and analyse the loss cultivates flexibility that allows us to move forward and gain additional wisdom.
3. Beginner’s Mind
The best learning results from the kind of openness a child has when learning to crawl — fully awake to the experience, receptive to gaining even tiny insights, refining one’s method in response. An inner willingness to adopt the nonresistant approach of a beginner manifests outwardly as forward movement.
4. Using Adversity
Rather than deny or stifle emotions when facing adversity, we must work to understand them, make peace with them, and ultimately channel them into higher levels of performance.
5. The Internal Solution
If we can prevent ourselves from being thrown by heightened emotions and instead learn to flow with them, the physiological responses they produce can help us defeat obstacles. We must first develop understanding and tolerance for inner turmoil, then transform it into creative inspiration.
6. Peak Performance
The power of presence. We enrich our experience of life by attuning ourselves to its subtlest aspects and delving deeply into its details. To excel, our perspective must be that everything is on the line at all times.
7. The Soft Zone
We should not brace against disruptions but rather adopt a nonresistant attitude. This allows us to absorb information, process it smoothly, take appropriate action, and grow. We become resilient like a flexible blade of grass surviving hurricane-force winds.
8. The Downward Spiral
When we cling to troubling emotions from an obstacle or loss, we abandon the present for the past. We must stay cool under fire and fully in the present to glean the most from every experience.
9. Stress and Recovery
By alternating cycles of rest with activities that push us to the outer limits of our abilities, we strengthen the bond between mind and body that fuels peak performance. The practice of stress and recovery should be incorporated into everything we take on.
10. Building Your Trigger
Identify the one key activity that is most relaxing for you. Shape a routine of four to five personal relaxation methods. Practice daily for one month. Then use the routine before high-stress activities. Gradually condense the routine until you can produce its benefits by merely thinking about it.
11. The Art of Introspection
Themes that arise in one area of our lives will surface in others — all aspects of life are interconnected. By bringing awareness to the threads connecting mind and action, we can break down walls between disparate parts of our lives and transform weaknesses into strengths.
12. Listening First
The first step to artful teaching is tuning in to the essence of the student. It is critical to appreciate each individual’s unique learning style and natural voice. Teachers who position themselves as guides rather than omniscient authorities promote a lifelong hunger for learning.
13. Loving the Game
To learn and perform at higher levels, we must reconnect to childhood experiences when our natural approach to discovery was light-hearted. At the core of success lies the journey from childhood back to childhood again.
14. Breaking Down Walls
It is vital that we unearth the psychological patterns and emotional responses that get in the way of our successes and take our weaknesses on.
15. Intuition
To truly excel, we must cultivate access to intuition — the bridge between the conscious and unconscious mind. We achieve this by alternating deep, repetitive study with periods of rest and relaxation.
16. The Middle Way
We must engage in a process that pushes us to the outer edges of our abilities, yet does not stretch us so thinly that we break down. We allow the bar to move a bit higher with each step along this balanced middle road.
17. Master the Fundamentals
It is most effective to launch into learning by studying a discipline’s most fundamental principles. A devotion to mastering nuances of basics builds the foundation required for more complex understanding and creative bursts of inspiration.
18. Learning the Macro from the Micro
Our approach to learning must emphasize depth over breadth. We have to dive deeply into small pools of information to explore the operating principles. Study the micro in order to learn what makes the macro tick.
19. Numbers to Leave Numbers
By studying discrete pieces of information thoroughly and practicing their application repetitively, they shift from the conscious to the unconscious mind where they connect with other chunks of internalized knowledge and manifest as the sudden burst of insight we experience as free-flowing intuition.
20. Bringing It All Together
Delve into essential aspects of foundational information in a manner keeping with your unique learning style. Devote yourself to exploring ever more advanced techniques at the outer edges of your ability. Alternate pushing yourself with periods of rest. Your internalized knowledge will lead to bursts of insight, which you can expand by breaking down the mechanics that led to your achievements.
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“A key component of high-level learning is cultivating a resilient awareness that is the older, conscious embodiment of a child’s playful obliviousness. This journey, from child back to child again, is at the very core of my understanding of success.”
Resources
Josh Waitzkin’s work has profoundly shaped how I approach coaching. The principles of depth over breadth, unobstructed self-expression, and living at your stretch point — these aren’t abstractions. They’re the foundation of the work I do with CEOs, founders, and investors every day.