How to Master Any New Skill

6 Lessons on Learning to Learn from Naval Ravikant, Richard Feynman, and Robert Greene

The Internet provides millions of people with access to education. Access to knowledge is no longer a competitive advantage in today’s economy. Information is abundant.

As the world evolves at an ever-increasing pace, common skills becomes obsolete and new opportunities are created all the time. Technologists are automating personal finance and investing. Cryptocurrency is now a sizable industry with meaningful business and career opportunities.

In this environment, the ability to learn new skills quickly is scarce and valuable.

I have pivoted my career from finance to marketing. Started businesses ranging from a tech startup to a marketing agency. As many entrepreneurs do, I’m always launching side hustles — from selling stuff on eBay to growing my blog into a profitable business.

Along the way, I’ve had to learn many new skills ranging from standup comedy to poker. I’ve called it, “honing my “meta-skill-set” of learning.” Here are six strategies that have helped me learn each new skill.

1. Choose wisely.

Learning takes time. You’ll inevitably face failure and even boredom along the way. Robert Greene, the author of Mastery, shares his perspective on how to remain disciplined in the face of adversity:

“To really become an expert or master requires the infamous 10,000 hours, or even 20,000 hours — perhaps the difference between being a chess master and a grandmaster. To apply yourself to a field or to a problem for that long a time means there will inevitably be moments of boredom and tedium. Practice, particularly in the beginning, is never exciting. To persist past these moments you have to feel love for the field, you have to feel passionately excited by the prospect of discovering or inventing something new. Otherwise, you will give up.”

It’s important that you enjoy what you’re learning so that you can overcome setbacks over the course of achieving mastery. Furthermore, if you’re going to dedicate years to learning something, it should probably be something that will help you achieve your goals.

I believe that the feeling of “love” that Greene describes is achieved by a combination of cost-benefit analysis and enjoying the process. In other words, if you understand that learning will help you accomplish your goals and you enjoy learning it, you’re going to love it.

I also believe that enjoyment arises as a result of success. You’re not going to think that the game is fun when you’re losing. When you’re winning, however, you’ll have a blast! Learn to love the process of learning. Eventually you’ll achieve success and you’ll [at least] love that part.

Choose what to learn carefully before investing too much time or money. Learn skills that you are well suited to master and will help you achieve your goals.

2. Shrink your ego.

The most difficult part of learning something new is accepting that you need to learn. It’s difficult to acknowledge shortcomings. Instead of viewing not knowing the answer as a shortcoming, view it as an opportunity. The smaller your ego, the more room you have to learn.

As you start to gain some initial proficiency, you may think you have it all figured out. I’ve made this mistake several times. It’s critical to be aware of unknown-unknowns — things that you don’t know you don’t know. As Richard Feynman, a theoretical physicist known for his work in formulating of quantum mechanics and physics, said, “I’m smart enough to know that I’m dumb.”

The more you learn the more you realize how much left you have to learn. No matter how much success I’ve achieved with a given skill, I never really feel a sense of mastery.

Rather, I simply realize that my former self — who thought he knew everything — didn’t actually know anything. When that thought crosses my mind, I know that I’ve learned something.

3. Learn the rules — so that you know how to break them

There are three levels of learning: rules, strategies, and counter-strategies. Learn the rules first. Then, learn the strategies of the people who have achieved the results that you want to achieve. Lastly, learn how to develop strategies for countering your opponents’ strategies.

Let’s walk through these three levels using baseball as an example. The rules state that the team that scores more runs after nine innings wins the game. You can swing a bat to hit the ball, but the bat can’t be made of metal, it has to be made of wood.

A common strategy is to put batters with a high on-base percentage at the top of the lineup, and power hitters who can hit them home immediately following.

In Moneyball: The Art of Winning an Unfair Game, Michael Lewis told the story of how the Oakland Athletics “broke the rules” by taking a data-driven approach to building the team.

The team’s General Manager, Billy Beane, discovered that teams overvalue players who hit home runs and undervalue players who get on base more frequently, even though getting on base frequently contributes to runs, which contributes to wins.

Their counter-strategy, then, was to sign players with a high on-base percentage and save money as a result.

Once you understand the rules, and how your opponents think about the them, you can find ways to break the rules.

In poker, you can “bluff” — make a large bet even though your hand isn’t likely to be better than your opponents — in situations where you know it will be difficult for your opponent to make the call. Don’t conflate knowing the rules of the game knowing how to win the game.

4. Practice trumps theory

You might think you’re good at something, but you really don’t know until you’ve put your learning to the test in a real world setting. Everything changes when you there are consequences for your actions — costs of losing and benefits of winning.

Your emotions boil up and you discover that, in practice, things turn out to be different than the books described. Mike Tyson said it best: “Everybody has a plan until they get punched in the face.” Here’s a funny video that illustrates this point in the context of investing in a demo account versus investing with real money:

Theories that make sense conceptually don’t always play out as you would expect in the real world. In these cases, evidence trumps theory. If you had told me two years ago that if our President were to nickname a foreign leader “little rocket man” and fire off typo-ridden Tweets about him that it would cause nuclear war, I definitely would have believed your theory.

In practice, however, we can see that not only has this unconventional approach not caused nuclear war, but actually brought us closer to achieving peace in North Korea than ever before. (Disclaimer: There are many reasons to criticize Trump, I am only using this as an example because it illustrates the point.)

This is why you need to practice —and practice frequently. Start practicing before you feel “ready.” Failure is an opportunity to learn.

In school, getting the wrong answer on a test is bad. In life, making a mistake is one of the best opportunities to learn and iterate.

Get obsessed with what you’re learning. Repetition is critical. There are no shortcuts. You have to put in the work.

5. Learn the principles and intangibles

While it’s important to the learn rules, strategies, and details, of any given domain, there are several frameworks and models that are critical to achieving success in almost any context. Here are a few:

Furthermore, while knowledge is power, there are many intangibles and skillsets that are critical to achieving results in almost any field. Here are some of the most important:

  • Overcoming fear of failure
  • Self-discipline
  • Communication
  • Nutrition and fitness
  • Self-awareness

Learn these models and skillsets to enhance your ability to learn almost anything.

6. Measure progresss in terms of the process — not the outcome

Sometimes it’s hard to tell if you’ve truly learned something. It can take years to start a business and achieve profitability or a successful exist. Some games have a low probability of success.

A venture capitalist may invest in ten startups over the course of several years. Eight or nine of them are likely to fail and only one or two of them is likely to succeed, but those one or two successes yield returns great enough to make the portfolio profitable.

Poker has a similar dynamic to venture capital. Daniel Negreanu, the second highest earning professional poker player of all-time, video blogged his experience at the 2018 World Series of Poker.

He played in 32 events for a total buy-in amount of $1,505,000, but didn’t win a single one of them. By the end of the series, here lost a total of $1,393,897! However, before the World Series began, he took 2nd place in a tournament and earned $3 million.

Sometimes you play well and still lose. Similarly, success does not mean that you did it right or that you don’t have more to learn. Naval Ravikant, CEO of AngelList, emphasizes the importance of maintaining a “beginner’s mind”:

“Success is the enemy of learning. It can deprive you of the time and the incentive to start over. Beginner’s mind also needs beginner’s time.”

Keep your ego in check when you’re winning and don’t get too down on yourself when you’re losing. Just keep learning and doing.

Find ways to get feedback along the way. Set short-term goals, understand the amount of outcome variance in what you’re learning, and be realistic about the results that you can achieve at each step along the way to achieving mastery.

Mike Fishbein studies the business and personal development strategies of world-class performers and shares how you can apply them to your life and work. Join 25,000+ readers and find his most popular articles at