Book Review: The Art of Learning

Rating: 📈

A self help book usually acts like a manual for achieving above-average levels of success, wealth, positive mental state, etc., told through parables of the author’s life.

What qualities do we find distasteful in self help books?

  • taking it as a given that everyone should uncritically strive to dominate and win within a conventional framework of success
  • claims that you, yes you, can dominate, win, and succeed like the author if you just follow these steps
  • encouraging exploitation of others in order to win
  • pushing pseudoscience, a la “Scientists hate this one simple trick” (positive thinking, law of attraction, etc.)

The Art of Learning: An Inner Journey to Optimal Performance by Josh Waitzkin, former U.S. Jr. Chess champion and Tai Chi Push Hands 2004 world champion, is a very good self help book. It manages to avoid the aforementioned obnoxious tropes and effectively communicate a lot of value to the reader in a humble, relatable, and actionable style.

In a 2007 interview, the year of the book’s release, Waitzkin talks about his distaste for the word prodigy and then summarizes his book in the same breath:

I think anybody can become tremendously successful at what they do as long as they approach the learning process in a way that isn’t self paralyzing. It’s my hope that my book helps pave the way for them to do that.

In the least charitable interpretation, what is Waitzkin doing here? Maybe he knows that his natural ability had a tremendous amount to do with his success. But he couldn’t sell the message “unless you’re born talented, you’re probably out of luck” to a broad audience, so he reframes it as “you too can be just like me!” to make a buck?

But that’s far from the story he tells in the book. Waitzkin admits to being born with talent and good instincts. But he also continually emphasizes the intensity of his training, intentional learning processes full of reflection and adjustment, emotional tumult, cultivating love for the craft and process, the role of decompression, and gratitude for the support of his friends, family and teachers throughout. Prodigy isn’t enough and it’s far from the whole story.

If one were to stick with the theory that success derives from natural abilities, then along with natural skill in a domain, the natural ability to learn, i.e. develop further skill in that domain, matters at least as much.

Waitzkin’s thesis is that learning can be learned, and that learning has similar enough qualities across disciplines that it’s worth talking about as a standalone skill to be cultivated.

Each chapter describes an element of learning, building towards a complete view of what it takes and feels like to learn effectively. Some of my favorites:

Two Approaches to Learning

This chapter is analogous to fixed and growth mindsets, but Waitzkin frames it as entity or incremental theories of intelligence. If you believe you can learn progressively and incrementally, you will, and if you believe you have a given skill set - even a talented one in relation to your peers - you will stay there and stagnate.

The key to pursuing excellence is to embrace an organic, long-term learning process, and not to live in a shell of static, safe mediocrity. Usually, growth comes at the expense of previous comfort or safety. The hermit crab is a colorful example of a creature that lives by this aspect of the growth process (albeit without our psychological baggage). As the crab gets bigger, it needs to find a more spacious shell. So the slow, lumbering creature goes on a quest for a new home. If an appropriate new shell is not found quickly, a terribly delicate moment of truth arises. A soft creature that is used to the protection of built-in armor must now go out into the world, exposed to predators in all its mushy vulnerability. That learning phase in between shells is where our growth can spring from. Someone stuck with an entity theory of intelligence is like an anorexic hermit crab, starving itself so it doesn’t grow to have to find a new shell.

I can deeply relate to this hermit crab analogy. Whether it’s been changing careers, switching jobs, taking on a new project in an unknown domain, investigating a new relationship…the transitional periods for me are always the most intense and filled with growth.

Loving the Game

In this chapter, Waitzkin talks about the balance between drive to win and succeed and the desire to focus only on what you love about an activity.

I have seen many people in diverse fields take some version of the process-first philosophy and transform it into an excuse for never putting themselves on the line or pretending not to care about results. They claim to be egoless, to care only about learning, but really this is an excuse to avoid confronting themselves. This issue of process vs. goal is very delicate…

While a fixation on results is certainly unhealthy, short-term goals can be useful developmental tools if they are balanced within a nurturing long-term philosophy. Too much sheltering from results can be stunting.

Waitzkin talks about his own departure from competitive chess in these terms:

I became alienated from chess somewhat. The external pressures of the film [Searching for Bobby Fisher] coming out, the spotlight, the need to win to win to win all the time as opposed to the freedom to explore the art more and more deeply, I think that that started to move me away from the game.

I see this tension in myself and my peers. When one intentionally doesn’t prepare for an interview or presentation as a hedge against the pain of a negative outcome, I think this is may be an indicator of a false and harmful story about “egoless, process-driven” mindset. When I spend time checking metrics of success – view or install counts, comments, etc. – rather than losing myself in further developing the thing that may have generated the engagement, this links outcome to process, and may contribute to me losing love for the game.

Beginner’s Mind

Beginner’s mind “refers to having an attitude of openness, eagerness, and lack of preconceptions when studying, even at an advanced level, just as a beginner would.”

I am at a point in my career where I have developed Opinions™️ about things. I am finding it dangerous. I’m invested in these opinions while also knowing that I have so far to go on the road to mastery. I have to be active about seeking out learning, actively working against the desire to sit comfortably on my hoard of existing knowledge.

Waitzkin describes his experience delving in to Tai Chi as a complete beginner, and the freedom that comes with new beginnings. It’s a good reminder for me to always try new things and be bad at them without ego, so I can bring that mindset back to the things where I have developed viewpoints that may limit my growth if left unmediated.

Investment in Loss

This may be my favorite chapter of the book. I have lost so many times in my life. By design, we remember losses much more potently than wins.

But Waitzkin, throughout the book, emphasizes the value of examined losses, and the lack of growth that comes from being a big fish in a small pond.

If a big strong guy comes into a martial arts studio and someone pushes him, he wants to resist and push the guy back to prove that he is a big strong guy. The problem is that he isn’t learning anything by doing this. In order to grow, he needs to give up his current mind-set. He needs to lose to win. The bruiser will need to get pushed around by little guys for a while, until he learns how to use more than brawn…Investment in loss is giving yourself to the learning process.

Replace “strong guy” and “martial arts” with “full stack web developer” and “game designer”, or “surfer” and “kite surfer”, most identity-activity pairs, really, and the connection to loss as an inevitable step on the road to growth is clear. And even when you’re really good at something, the path to improvement is still through loss – this is what the beginner’s mindset helps facilitate. I’m reminded of the quote about cycling: “It doesn’t get any easier, you just get faster”. Losing is painful, but without it there is no growth at any level.

It is common knowledge that Jordan made more last-minute shots to win the game for his team than any other player in the history of the NBA. What is not so well known, is that Jordan also missed more last-minute shots to lose the game for his team than any other player in the history of the game. What made him the greatest was not perfection, but a willingness to put himself on the line as a way of life.


There is a lot more to talk about with this book. I really recommend reading it if you care about tactical development in pretty much any discipline. For me right now, that’s still primarily software, surfing, and investment in my relationships.