The Best Book for Understanding Mastery

Norm Wright

Published in

Striving Strategically

15 min readNov 3, 2018

Mastery

By Robert Greene

Rating: 10/10

Best Line #1: If it is money and comfort that dominate our decision, we are most often acting out of anxiety and the need to please our parents.

Best Line #2: No good can ever come from deviating from the path that you were destined to follow.

Why Read About Mastery?

If you check the Amazon reviews for Mastery by Robert Greene, you’ll find people writing a lot about how the book had an immediate, positive impact. Greene’s insights helped them improve, increase confidence, and find new levels of success. Some even write that the book helped them discover their purpose.

Cast in such light, you might think Mastery is a self-help book.

After all, the message from the first line of the dust jacket is very uplifting: “Each one of us has within us the potential to be a Master.” This is true. So rejoice! You, too, can be a master!

Or something else. You can be a master of a craft or wealthy business tycoon or a head of state or a standard-issue suburban parent or a Buddhist monk. So why choose mastery?

What is it that drives people to this topic?

For me and many others, it begins in 2008 with the publication of Outliers by Malcolm Gladwell. Soon after, talk of the 10,000 hour rule spread like wildfire. At last! We had uncovered the recipe for becoming really great! You didn’t have to be a genius. You weren’t just born with some special gift that no one else could attain. You just needed to spend 10,000 hours on something.

Other books followed, each emphasizing the importance of deliberate practice and time. Such books include Talent Is Overrated by Geoff Colvin in 2008, Drive by Daniel Pink in 2011, and then Mastery in 2012. Many other books on the topic are scattered in-between. The outburst of this literature ended (maybe?) in 2016 with a book by the original researcher on the 10,000 hour rule. The book is called Peak and it’s a fine read.

All of them are. I have read all these books. It’s amazing how much knowledge there is on the topic. Robert Greene’s Mastery is the best of the bunch. And yet, these books have done nothing to make me more of a master. I read each with intense interest and never really progress the way I’d like. It reminds me of an Einstein quote:

Reading, after a certain age, diverts the mind too much from its creative pursuits. Any man who reads too much and uses his own brain too little falls into lazy habits of thinking.

I think this is a bit harsh but the idea is still strong: those books didn’t help me gain anything but knowledge and knowledge that isn’t put into practice is, well, kinda useless. Does that mean you should stop reading this article and go back to your deliberate practice? Probably! But before you go, let’s cover a little more ground. First, consider the core findings covered in this week’s posts:

These articles have one thing in common: they are bearish on Mastery. I’m not sure it’s the sort of thing that the bulk of Greene’s audience really wants. I think we all want growth; we want to acquire skills; we want to be successful. But mastery? True mastery has an incredibly high price. It requires an intensity of effort, over lengthy duration, that few can hold. Because it’s actually more like an uncontrolled obsession than a willful commitment of energy.

Consider this line from Page 12 of the book:

And at the core of this intensity of effort is in fact a quality that is genetic and inborn — not talent or brilliance, which is something that must be developed, but rather a deep and powerful inclination toward a particular subject.

Genetic and inborn. What intensity of effort do you hold that is genetic and inborn? Whatever it is, I imagine it is so great that you don’t need any literature on mastery in order to capitalize on it. You’re already so focused that reading books on the topic is a waste of time.

And if you don’t have such a genetic, inborn intensity already, well, reconsider the journey towards mastery. As Greene explains two pages later:

First, you must see your attempt at attaining mastery as something extremely necessary and positive.

“Extremely necessary”. I take that to mean that attaining mastery is “the most important aspect of your life.” I know this is true for most, if not all, the masters featured in his book.

With this in mind, an earlier version of me would really dislike the suggestion I’m about to make. This is because an earlier version of me very much wanted to be a master of something. Because being a master felt like a one-way ticket to a straight, easy path in life. An extremely necessary goal would mean no more rethinking my choices, my direction, my trade-offs. Everything would be for the craft and I’d move into autopilot, pushing myself towards world-class status in one specific thing. Get Great Or Die Trying. That was the only approach that I thought mattered. That was before I discovered another way.

Put simply, the old me, pre-2018, believed very much in the notion of a Jack-of-all-Trades, Master-of-None. It seemed easier.

Today, I believe in another (better?) way: Jack-of-all-Trades, Master-of-One. It goes back to the thesis of Scott Adams’s book that a couple good skills are better than a single great skill. Good + Good > Excellent. It seems more interesting.

Finding The Path. Adhering To It.

Why is it more interesting? Well, because it fits my path. It may be terribly uninteresting to you and this is a central point of Greene’s book. He is deliberately vague and wide-ranging in his examples of mastery. Polymaths like DaVinci are compared with the more-focused brilliance of Einstein. This illustrates that mastery takes many forms. It must. We’re all different people in different circumstances.

So in the early portions of the book, Greene provides terrific insights into why this matters. An important sequence involves the life of Buckminster Fuller. It starts with a line that is crucial for us to never forget, whether we seek mastery or not:

No good can ever come from deviating from the path that you were destined to follow.

Greene illustrates this truth with a beautiful exposition on Buckminster Fuller that, alone, is worth the price of the book. You really should read it, especially if you find yourself in a situation where you feel you’re drifting away from what you should be doing. It closes with a number of lessons, one of which is best expressed in the line below:

There is no compromise here, no way of escaping the dynamic. You will recognize how far you have deviated by the depth of your pain and frustration. You must listen to the message of this frustration, this pain, and let it guide you as clearly as Fuller’s voice guided him. It is a matter of life and death. The way back requires a sacrifice.

There are plenty of people who have argued the idea that we should not be ruled by our passions. But what else could possibly rule us?

Cal Newport is one of the more persuasive on the topic on not being ruled by our passions. In his book “So Good They Can’t Ignore You”, he argues that there is a passion mindset and a craftsman mindset. I think he misunderstands the relationship here. These are not separate mindsets. One infuses the other. You don’t either follow your passion or follow your craft. You cultivate an initial passion, a natural inclination, through the craft, perpetually motivated by the minor success it brings and thus stoking the passion even more. Can you become “so good they can’t ignore you” by Newport’s approach? Sure. But I don’t think that’s what we see at the level of mastery. Newport’s guidance can make you successful, I’m sure, but it won’t make you a master.

Put simply, if mastery is the goal, no one becomes a truly great master without passion. Hell, I argue that it’s more akin to addiction. Masters are not selfless craftsmen who, as Newport argues, “see what they can give the world.” No, they are dominated by an all-consuming curiosity that is quite self-indulgent.

Put simply, you can only master that which you innately desire as your Life’s Task based on what you are inevitably good at. Anything outside of that can be good, perhaps even great, but it won’t be mastery. Regardless of the 10,000 hour rule.

Life Is Short. Follow Your Passion. Whether For Mastery or Not.

Greene understands what many people have yet to really respect: you may choose to not follow your passions but your passions will always follow you. You cannot hide from them. And every time you try to subdue them for a paycheck, prestige, social acceptance, or the pleasing of your parents, you will feel the pain. I know this from experience.

When we open ourselves to this reality, it produces an amazing truth: there is some internal compass that points us in a particular direction. Call it your “gut” if you want. We can ignore this compass but the magnetic pull is always there. If we do ignore it, it becomes the stuff of our dying regret. People truly carry this magnetic pull to their deathbed. Bonnie Ware, a palliative care professional, has written extensively on the topic of dying and has said the most common regret of those dying is that they didn’t “live a life true to themselves.” They did what others expected of them. They failed to follow their path.

The path beckons at all time. Even when near the end.

So what is our path? It’s seldom clear but consider what inhabits your mind the most. Assuming you’re clothed, fed, and secure, your mind will move quickly to a core set of elements that help light the direction. As Greene says,

It is a simple law of human psychology that your thoughts will tend to revolve around what you value most.

What you think of the most consistently (not indulgently, not hedonistically, but consistently) is a beacon towards your path. Many of us, myself included, value growth above all. This is a blessing and a curse. No one can become a master at growth, per se. This creates real difficulty in reconciling what, exactly, our mastery can be.

Specialization Is For Insects. Why Classic Mastery is Fragile.

A human being should be able to change a diaper, plan an invasion, butcher a hog, conn a ship, design a building, write a sonnet, balance accounts, build a wall, set a bone, comfort the dying, take orders, give orders, cooperate, act alone, solve equations, analyze a new problem, pitch manure, program a computer, cook a tasty meal, fight efficiently, die gallantly. Specialization is for insects.

— Robert A. Heinlein

Many people have told me I should get a PhD. It’s a deeply-valued compliment that I always appreciate. The only trouble is that I’ve never loved a single subject — even writing — enough to go through that gauntlet. For quite some time, this made me feel like a failure. What will I have to show for my intellect and ability if I wasn’t a deep expert, a PhD, in something?

The question haunts me on occasion. Until I read lines like the one from last week’s book review on Factfulness. There is a line Hans Rosling wrote that dispels my insecurity for the time being. In the section on the “single perspective instinct”, Rosling talks about the limits of experts. Experts are quite useful in their field but cannot be relied upon outside those bounds. It’s the same dynamic between the fox and the hedgehog, a classic concept developed by Philip Tetlock. The fox is akin to the multi-model thinker, an intellectual mixed-breed mutt in the cognitive kennel, and is always more resilient than the lone hedgehog specialist with their rigid fixations.

What makes someone a fox over a hedgehog? I think it’s the desire to integrate and synthesize many views, to love complexity rather than attempt to kill it with simplicity, to desire forward movement over being right, and to welcome correction. Hedgehogs do the opposite. They adhere to one great body of knowledge that occupies their sole focus. They have one solid lens, a telescope, and in Tetlock’s studies, this telescope is naturally quite accurate at long-term prediction. Foxes, however, have many other lenses that they switch with ease. As a result, foxes are more accurate than hedgehogs at short-term prediction. By a significant margin.

Foxes aren’t pundits. Hedgehogs are. Foxes aren’t typically viewed as experts. Hedgehogs are. Foxes don’t become scientists. Hedgehogs do.

Pundits … experts … scientists … Those seem to resemble the classic picture of mastery. How can someone be a master if they aren’t a hedgehog? (sidenote: this is a very funny question if someone read it with zero context.)

This is the question I asked myself all week. A good question. And the wrong question.

All week long, I kept thinking of mastery through the notion of skill acquisition. Stephen King the writer. Einstein the physicist. Edison the inventor. Their skill is tangible, applied, and discrete. You can demonstrate it cleanly and easily within its specific domain.

But there are metaskills, of course. Genuine abilities that can be improved over time. Learning is a metaskill. Language is a metaskill. Persuasion. Analysis. Memory. This is the stuff of the Heinlein quote that starts this section. If we can learn how to learn, how to bend language, analyze situations and provide persuasive, memorable experience … if we can do that, we can do all the things Heinlein suggests. Jack of all trades, Master of One. Skill layering at its finest.

So maybe that’s where mastery lies for the foxes of the world? In skill layering? And the collection of multiple models? Perhaps.

Truth be told, I don’t think that’s the ground truth. And so now, after more than 7,000 words over 5 essays, I find myself exhausted and only somewhat convinced that I’ve hit paydirt.

The lessons of this fine book aren’t about achieving mastery in a skill.

The lessons of this book are about achieving mastery over one’s self.

Not very profound, I know. But every aspect of this book points to the ways in which our natural, short-term inclinations stand in the way of transcendence. Part One is about the way we fail to accept our desires, our inclinations. It details the way in which we tragically abandon the true path and the Life’s Work. I’ve quoted several lines this week on how we seek comfort and conformity over the pursuit of our innermost values.

Part Two and Three, which I covered with some skepticism, focuses on the journey through apprenticeship and the need for mentors (or, I think, the need for audiences instead).

Part Four relates to social intelligence and the ways we must adjust our attitudes and approaches to others so that our abilities can be received.

Part Five covers the un-intuitive way in which we must break all the rules we have relied upon.

If you would like a more detailed summary of these sections, visit Nat Eliason’s post from last year. But be forewarned: it won’t get you any closer to mastery. It’s the recipe, written as a full reference document, but it doesn’t make you the chef. I and many others have cataloged this information but I think the mere information skates past the real point.

The Mastered Self

We stand in the way of our mastery. We cannot be masters until we allow ourselves to be mastered. Again, I called this addiction in a previous article but it might not be so callous as that. Jocko Willink, the rising star of Navy Seals fame, is a master. Of what? Well, combat, I suppose. But much more importantly, I think he’s a master of his fears. A master of his self.

When you really read Greene’s book and really look past the perfunctory “how-to” parts that rhyme with every other self-help book out there, what you find is a suggestion for a particular state of mind. It reminds me of Josh Waitzkin’s book, The Art of Learning, but Green goes much further in explaining the obstacles and means to avoid them on this journey.

It starts with avoidance of the rational mindset. In the beginning, the rational mindset is what pushes you towards convention, the safe bets and repression of your true desires. You must overcome that. You must abandon this more rational, emotionless aspect of your mind and hold tightly to the joy that comes with the work you do. From page 177:

Masters and those who display a high level of creative energy are simply people who manage to retain a sizeable portion of their childhood spirit despite the pressures and demands of adulthood. This spirit manifests itself in their work and in their ways of thinking.

Doing this, you can complete the first 50% of the journey. Then a new obstacle emerges. The joy can turn to conviction and you can become rigid, absolute, and orthodox. From page 231:

In order to learn a subject or skill, particularly one that is complex, we must immerse ourselves in many details, techniques, and procedures that are standard for solving problems. If we are not careful, however, we become locked into seeing every problem in the same way, using the same techniques and strategies that became so imprinted in us.

You must then return to the more rational elements of your mind to regain your skepticism, your mechanical approach of trial and error and a rooted sense of fact. There will be tension here, between your emotional conviction and your factual evidence. This is where the next step to mastery lies, exploiting those tensions for something new, something greater that only you can uncover. This is your product, not the knowledge and technique others gave you. From page 248:

Your task as a creative thinker is to actively explore the unconscious and contradictory parts of your personality, and to examine similar contradictions and tensions in the world at large. Expressing these tensions within your work in any medium will create a powerful effect on others, making them sense unconscious truths or feelings that have been obscured or repressed.

Then comes the transcendence — part six of Greene’s book, the fusion of the intuitive with the rational. This is a very deep, rich, and beautiful conclusion. It simply must be read. In this final portion, I came to understand how mastery is truly more about the mastery of self and environment more so than a skill. In fact, by this part of the book, skills almost seem like some sort of silly appendage, rudimentary things that the paragons of progress wield like any other tool. Here it becomes more about the synthesis of said skills. Masters weaves these skills together in the right environment to create something great, be it an object or an experience.

Again, this part focuses solely on mastery of self. Because the self is all that remains as the obstacle. As Greene writes on page 297:

Mastery is like swimming — it is too difficult to move forward when we are creating our own resistance or swimming against the current.

That sounds like New Age psychobabble until you read the book.

Conclusion

This is a very hard topic for me. And a very hard book to definitively interpret. I have a love/hate relationship with the pursuit of mastery. Many days, it fills me with a tremendous sense of purpose. I want to be a better writer, leader, manager, decision-maker, thinker, etc. So I design my days accordingly.

But I realize the massive insecurity this effort creates; even when you give yourself the patience and time that Greene wisely counsels, you can’t shake the constant desire to improve. You want to improve because you’re never good enough; you’re never good enough because you want to improve. It’s a vicious cycle.

Want to make someone miserable? Tell them they can be anything they want to be. This creates an immediate pressure to be everything. Which often leads to being very little.

It was in that frame of mind that I expressed skepticism on the topic all week. Mastery is overrated. Why try for it?

But consider the guy who writes that question. It is the same guy who runs a publication called “Striving Strategically”. It is the same guy who is writing the final touches on the Friday book review at 9:26 pm because I can’t break my streak of consecutive business days publishing an article. It is the same guy who can’t stop learning and synthesizing.

Master is genuinely overrated. It may even be antithetical to living a good life. And yet I don’t think I’ll ever stop striving for it. I simply can’t let it go. That’s the core ingredient for making it possible. But just because it’s possible doesn’t mean it’s guaranteed. So the work continues. The work always continues.

You can buy a copy of Mastery here. It’s highly recommended.

Mental Models and Principles

Mastery has two core ingredients: time and desire.
Intensity of effort is genetic, inborn. It comes from a deep, powerful inclination toward a particular subject.
Your true lack of desire catches up with you.
People get the mind and quality of brain that they deserve through their actions in life.
If it is money and comfort that dominate our decision, we are most often acting out of anxiety and the need to please our parents.
The greatest mistake you can make in the initial months of your apprenticeship is to imagine that you have to get attention, impress people, and prove yourself.
Your thoughts will tend to revolve around what you value most.
When it comes to mastering a skill, time is the magic ingredient.
Of seventy great classical composers, it took ten years to produce their first great work.
The Conventional Mind is passive — it consumes information and regurgitates it in familiar forms.
The Dimensional Mind is active, transforming everything it digests into something new and original, creating instead of consuming.
There is nothing that becomes repetitive and boring more quickly than free expression that is not rooted in reality and discipline.
People are dying for the new, for what expresses the spirit of the time in an original way.
Fuse the intuitive with the rational.
You must see every setback, failure, or hardship as a trial along the way, as seeds that are being planted for further cultivation, if you know how to grow them.
Those qualities that separate us are often ridiculed by others, or criticized by teachers.
People do not advertise their rigidity. You will only trip up against it if you try to introduce a new idea or procedure.