The Ultimate Cheat Sheet To Mastery

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Are you satisfied with your life? Do you go to work knowing you could do better?

Knowing there are unique talents in you that could make you great, the best in the world?

This post is about achieving mastery. But also why it’s ok to not get mastery in the traditional sense. You can define it, not use the definitions provided by everyone else.

In other words, it’s fine to be a loser.


There are a lot of books written on this topic. If you want to read an entire book on it, read Robert Greene’s “Mastery” (or watch my podcast with him). There’s also “Outliers” by Malcolm Gladwell.

But it’s not that hard. It doesn’t take a book to describe what makes a master. For one thing, most of us, and I mean me, will not be masters at anything.

I try. I tried with chess. I hit the rank of “master” but that doesn’t mean anything. I’ll never be world class at it. I’ve tried with writing. I’ve been writing for twenty or so years.

But I’ve known a lot of people who are among the best in the world in their field. I’ve read all the books. I’ve talked to all the people and dissected what they thought led them to their mastery.

I’ve built and sold businesses to people who were masters of their fields in every industry. I’ve invested in people who were masters in their fields.

So I’ve at least recognized who were masters and what they did.

Take this then with a grain of salt but based on my experience and the experiences of all the people I’ve interacted with.

Here are the elements of mastery. I also have some good news and bad news.

A) TALENT.

I hate to say it, but talent is a factor.

There’s a myth that everyone is talented at at least one thing and you just have to find it.

This isn’t true.

Most people are not talented at anything. Most people can be pretty good at something. For instance, Tim Ferris shows in “The Four Hour Chef” how you can be a pretty good chef with four hours worth of work.

I’ve tried his techniques and in four hours I made some pretty good dishes. Thank you, Tim. But at the launch of Tim’s book he held a dinner where each course (I think there were eight of them) was cooked by a different chef.

One of the chefs was (approximately) eight years old and his dish might’ve been the best served. That kid will be a master one day if he isn’t already. That’s talent.

When my chess ranking was peaking back in 1997 I played in a tournament against a girl fittingly named Irina Krush.

She really did crush me in about 25 moves. After the game she told me, “Maybe your bishop to B4 move felt a little weak to me.” She was right.

She was 13 years old. I stopped playing chess in tournaments right that moment and now only play when I’m on the phone with people. She had talent. She’s now one of the youngest women grandmasters in the world.

B) HOW DO YOU FIND what you are talented at? I think there are roughly two methods.

i) Take out a pad.

List everything you enjoyed doing from the ages of six to eighteen, before your life was ruled by college, relationships, crappy jobs, mortgages, kids, responsibilities, self-loathing, etc.

I was talking to Lewis Howes on my podcast. He mentioned he always wanted to be an athlete since he was a little kid.

He also mentioned that he used networking skills to help himself out even at an early age in order to deal with what seemed like poor academic skills. He found his two talents and became masters at both.

Often, it’s a combination of sub-talents that make you uniquely a master in that one field.

For me, I don’t know if I will master anything, but since I was a kid I loved writing, games, and anything to do with business. Maybe one day.

ii) Go to the bookstore.

Find a topic you would be willing to read 500 books on. If you can’t wait to read all 500 books in the knitting section then you probably have a talent at knitting.

Note that it is really ok to not be talented at anything. We weren’t put on this Earth to be talented at knitting.

Do you know why we were put in this Earth? I hope you know, because then you could tell me. But chances are there really isn’t any reason.

We ultimately are a combination of all of our experiences, all of the things we are interested in, all of the things we flirt with. And that combination might look like garbage to everyone else.

So play with your garbage and be happy. If you can do that, you’re in the top 0.00001%.

C) FOUR HOURS A DAY.

It’s not mystery Tim Ferriss’s books all start with “The Four Hour…” I ask almost every master I encounter, in every field, how much time per day do they spend mastering their field.

They did not give the standard Silicon Valley BS Entrepreneur answer: “I work 20 hours a day and if I didn’t need to sleep I’d work 30 hours a day”.

You can’t get good at something if you are working 20 hours a day. In fact, something is very wrong in your life if that is how much you are working at ONE thing.

The typical answer is: “I study four hours a day”. Anatoly Karpov, former World Chess Chamption, said the maximum he would study chess is three hours a day. That’s a guy who was a world champion.

Then, when he wasn’t in tournaments, he’d spend the rest of the day exercising, studying languages, doing other things to balance out his life.

D) HISTORY.

In any area of life you want to succeed at, you have to study the history.

All art is created in context. If someone wrote Beethoven’s Fifth Symphony right now it would be laughed at. It wouldn’t fit the current context of music, even though it would be a work of genius.

Andy Warhol tried many different areas of art before he decided that painting Campbell’s Soup Cans were the right art for the right moment in time.

In any sport, studying the history of how previous world champions played and trained is critical towards figuring how you can improve on that training and playing.

In any business, studying the history of that industry, the biographies of the prior executives, the successes and failures of those who went before you, is critical for mastering that business.

For example, I had Greg Zuckerman on the podcast talking about the current resurgence in oil drilling in the US. Everyone thought the US was out of oil back in the 1970s.

Well, now the fastest growing city in the United States is Williston, North Dakota and the US will probably be a net energy exporter by 2020. Heck, the one McDonalds in Williston has gone from $5 million in revenues to $18 million in revenues last year. The average McDonalds does $8 million in revenues.

If I were remotely interested in fracking I’d study where all the oil was drilled back in the 1920s, 1950s, 1970s. How the first wildcatters found their wells. What technologies were used. What’s the history of the technology. How were improvements made. What’s the history of the geopolitics around oil drilling. And so on. Somewhere in there there is a path to getting incredibly wealthy. Not for me, because I could care less about oil. But for someone. Or many.

E) STUDY YOUR FAILURES.

I was talking poker champ Ylon Schwartz. He’s won over $7mm in tournament winnings and untold millions in informal cash games. We grew up together playing chess until he made the switch first to backgammon and then poker.

I asked him why a lot of people play poker for 20 years but never get better. What’s the story?

He said, “everyone wants to blame someone. They want to blame bad luck. Or they had a fight with their wife. Or something. But the key is you have to study your failures. You have to take notes about your losing hands and even your winning hands. You have to think about everything.”

We spoke about another friend of ours who went from homeless to millionaire in six months once he found that he had a knack for backgammon.

His name was Falafel because at the time that was all he could afford to eat.

Ylon told me, “Falafel memorized every statistic about backgammon. Right now on the web you can see that his tournament games are ranked #1 in terms of how accurately they mimic a computer. Falafel also studied every single game he lost.”

I used to play Falafel every day in chess. He’d sleep on the ground in Washington Square Park and get up in the morning with dirt and leaves in his hair and we’d play chess for fifty cents a game. Now million dollar bankrolls from backgammon are normal for him.

F) EXPERIENCE.

At some point you have to cook 10,000 meals. Or play a million hands of poker. Or 1000s of games of chess. Or start 20 businesses.

Very few are successful right away. That would require too much luck and luck favors the prepared and the persistent.

In those 1000s of whatever you will encounter much failure. We all know that the best baseball players in the world are enormous successes if they strike out “only” 70% of the time.

When my dad died I went to his house and logged onto his chess account. I saw that he played about 30,000 games. He never got any better.

A lot of people can play the 10,000 hands of poker and never get better. Or bake 1000 cakes and never get better.

You have to remember your experiences, study your failures, try to note what you did right and what you did wrong, and remember them for future experiences.

Will future experiences be exactly like the old experiences? Almost never.

But you have to have the ability to say “Hmm, this is like the time four years ago when X, Y, and Z happened.”

G) PATTERN RECOGNITION

Being able to recognize when current circumstances are like an experience you had in the past or an experience SOMEONE ELSE you’ve studied had in the past is critical to mastery.

Pattern recognition is a combination of all of the above: study + history + experience + talent + a new thing…Love.

H) LOVE

Andre Agassi famously says he doesn’t love tennis. I believe this and I don’t believe it. We all know that there are all kinds of love. There’s unconditional love, which is very hard. The Dalai Lama can have unconditional love.

Then there’s lust. You look at someone and she is the Oomph to your Ugh. She is the BAM! to you BOOM! You dream and daydream and dream and daydream until the love is all worn out and six months or six years later it’s over and you move on.

Then there’s love that matures. There’s a set of things you like about a person, even love. Mix that in with some lust. Then this love mashup changes over time.

Or you learn to adapt because you know that a maturing love is not one where you settle or explore the subtleties inside the other person but you are finally able to explore the subtleties inside of yourself.

And sometimes you just fall out of love. There is no shame in this. Do what your heart tells you to do.

Some relationships are weird combinations of all of the above. They are tumultuous. There is much pain and much pleasure. Perhaps tennis was like that for Agassi. I can’t speak for him.

But to become a master at anything there will be much pain. And it can’t be avoided. Nobody has avoided it.

If something is too much pain, then it’s not the worst thing in the world to give up. I don’t like dental surgery. It’s too much pain for me. So my teeth are messed up a bit. I give up on having perfect teeth.

I) PSYCHOLOGY.

One reason most people in the world don’t get really good at anything is because they have no talent for anything that anyone cares about.

Another reason is they don’t want to put in the work. I understand this.

Often it’s better to be social and have friends and strong family relationships and love people.

Many people who have mastered something often have a hard time with their relationships with family members or spouses or friends. Van Gogh cut off his ear. Dostoevsky, Kafka, Bobby Fischer, Godel, were never known for their social skills and often were faced with depression, suicidal tendencies or borderline schizophrenia.

When you have a career, there’s this idea that you will go from success to success. You start in the cubicle, then you get an office, then a corner office, then you move horizontally into a CEO position at another company, and so on.

You might have some failures along the way but they won’t be big failures.

With mastery the one thing in common is that there are ALWAYS big failures.

With poker champ Ylon Schwartz, the day before he left for Las Vegas in 2008 where he won over $3 million I was with him, providing support for him in a court case. He had a court appointed attorney because he was dead broke and in debt.

He asked me that day, “I have to get on a plane for Las Vegas tomorrow and when I get back I could go to jail. How am I going to get through this?”

I didn’t have an answer for him other than the usual cliches. But he got on that plane. And every day he went higher and higher in chips. And he won $3.7 million in that tournament and hasn’t looked back.

A lot of people in the investing world don’t like Tim Sykes. He has a very arrogant marketing style. He’s a friend of mine and I can tell you he’s not that arrogant. He’s extremely humble. The reason he’s so humble is that he’s gone broke several times since his first success.

It’s no fun going broke. I’ve gone broke several times. You never go broke and think, “Well, it didn’t work this time, but it will work next time.”

You go broke and you think, “That was the worst experience in my life and I’d be better off dead. That was my last chance. It’s all over for me now. I’d rather be dead than go through this pain I’m feeling right now. And everyone around me would be better off if I were dead.”

That’s what you think.

And when Tim was making one of his comebacks, nobody would speak to him. I had him on some videos with the company I was working with but ultimately they banned him.

So he chose himself. He did all of the above. I’ve since looked at his audited track record and seen that he’s made millions from trading. I know 1000s of daytraders. 1000s. I know one successful daytrader and that’s Tim.

On the path to Mastery, everything will go wrong.

As Robert Greene points out in his book, “Mastery”, Napoleon got banished to Elba where he supposedly said his famous palindrome (somehow speaking English for the first and only time in his life) “Able was I ere I saw Elba”

Every master has his Elba. Banished to an island where the life you once knew no longer exists and it seems like there is no way to escape.

Napoleon escaped because he was the best in the world at what he does.

Because he had the psychology, or perhaps the blind spot, to not recognize that this was “it”, his final destination. Studying how he came back to power is a great example of psychology mixed with all of the above skills in becoming a master.

Tim went from millions to broke to trading out of his parent’s basement to millions again and this time he’s not going to fall back.

Bobby Fischer spent much of his life in borderline schizophrenic agony when he couldn’t deal with his losses. He’d disappear for years at a time but then come back stronger than ever.

How do you build that psychology? I don’t know. It’s a combination of many things:

– Ego. A real belief that you can be the best, against all possible rational evidence against this. Against everyone trashing you simultaneously.

– No way out. I asked Ylon, Lewis, and many others what were they thinking at rock bottom and the answer almost always was: “What else could I do with my life? I had to keep going!”

J) PERSISTENCE.

Add up all of the above and you get persistence. Persistence creates luck.

Persistence overcomes failure. Persistence gets you experience. Persistence is a sentence of failures punctuated by the briefest of successes, and eventually those successes will start to propel you towards mastery.

Not one success or two. But many many many.

How do you get persistent when life is filled with changing careers, relationships, responsibilities, economic crashes, historical upswings, and so many things that can get in your way.

There’s no answer at all. That’s why it’s called persistence. Because no matter where you are, there you are, doing what you always did. Not letting any of the above stop you. Using all of the above in your Mastery Arsenal to propel you to higher successes and deeper failures and then even higher successes.

It’s painful and brutal and no fun and nobody will ever understand why. And when you achieve success people will act as if it’s the most natural thing in the world to have happened to you.

And you try to explain, “No, there was this one time…” but they don’t want to hear it. They want to know what their next move should be so they can be where you are.

There’s no next move. There’s only your next move.

K) MYSTERY

Ultimately, Mastery = Mystery. You’re going to break the sound barrier on some field that nobody has ever gone that fast or that far. You’re going to find your own unique combination of passions that make you the best in the world at that combination.

What if nobody cares? That’s ok also. You care.

What if you never go for the mystery. What if you settle back into the known, the comfortable, the stress-free existence of your peers and colleagues and everyone you ever knew.

The world might not allow it. What you thought was comfortable might’ve been a myth also.

So you can only do this:

Ask: what can I do right now to move forward. Only this second. Having a goal in the distant future is almost a damnation of this moment in time. An insult.

We can’t predict the future. And the history of mastery shows that nobody was able to predict which goals would work and which wouldn’t.

Only this moment matters. Health-wise: physically, emotionally, mentally, and spiritually. Can you move forward today in each?

Then you will attract the mastery and the mystery.

* * *

THE GOOD NEWS:

You don’t have to be the master of the world. You don’t have to do any of the above.

Very few people do. And many of them experienced much hardship and pain along the way. And will continue to experience that hardship.

We live in a culture where it’s almost a damnation to be considered mediocre. But society has no clue about what real mastery is. Don’t listen to any of the “Top 10 things…” articles. Don’t listen to anyone. Not even me.

Freud has said that our two goals in life are human connection and achievement.

But often it’s a reasonable goal to overcome these evolutionary inclinations.

To be happy with your loved ones. To be satisfied for every gift in your life, for every moment, not rushing to the next moment of mastery. True mastery can be found right here, right now.

Choosing yourself right now in how you treat yourself, how you treat the people around you, how you treat your efforts and your loves.

Nothing is more important than this. Nothing compounds into greater happiness in life more than this.

Because when you rush to get to a mythical THERE, one day you will arrive and realize you missed all of the pleasures and mysteries along the way.