The Most Important Skill

The old retired version of you is a product of your decision-making.

The decisions you make, especially while young, will make or break your future. Every decision echoes through your life, bringing second, third, and fourth (etc...) order consequences.

Judgement is your proficiency in choosing the decision that gives the outcome you want. Judgement is knowing the long-term consequences of your actions.

Given this is such an important skill, how can we improve it?

Judgement is something gained from experience and self-reflection rather than books, or teachers.

Successful investors are good role models in this sense because they have a public track record of judgement that's paid off.

Judgement is domain-specific. Warren Buffett and Charlie Munger talk about their sphere of competence, which is the types of businesses they have experience working in or with.

These two famous investors only put their money in a small category of what's available. Contrasting this think of how most people invest, typically they'll just throw their money into a company and market they know nothing about.

It's closer to pulling the lever on the slot machine, because investing is such a multivariate space. They're throwing darts while blindfolded.

You gain judgement with time and experience. This is exemplified by Buffett and Munger only investing in what they consider their wheelhouse.

Gaining experience should be prioritized early in life.

Think of characters such as Conor McGregor who are characterized almost solely by arrogance. This archetype does surprisingly well. So what can we learn from this trait that is purported to be bad, yet seems to garner success?

Arrogance is a mixture of boldness and hubris. I argue the benefits lie in the former. Hubris is an emotional sense of superiority, and it's easy to see how this perverts judgement.

The 28th law in Robert Greene's The 48 Laws of Power is “Enter action with boldness”.

Boldness is defined as acting despite what others or yourself view as fear. This is highly linked to courage. Courage is acting despite your fear, and society acknowledges it as an admirable trait.

Every courageous action is bold, but not every bold action is courageous. Society doesn't outwardly praise boldness as a trait, but it rewards those who embody it.

It makes sense that society would reward an individual for doing something others wouldn't. Bold action is one of the best ways to gain practical experience.

Commit as many mistakes as possible, remembering only one thing: don't make the same mistake twice.

The world is chaotic, entropy is law. Any valuable experience you can gain is always through stepping into the unknown. When you're born, you're a blank slate. Naive because you can't know any better. It's only possible to improve judgement and wisdom through experience and learning. This is why the stereotype of a wise person is old.

The more mistakes you make, the better your judgement of what not to do. And what is success if not avoiding all mistakes?

Cynicism is the lazy answer. Going from naive to cynical does make you wiser, but it's not wisdom. You'll often be right when you adopt a cynical attitude, but your beliefs are sometimes self-fulfilling. Because you believe it won't work, it doesn't. What could be worse?

The better approach is to be contrarian. Most people think that means disagreeing with everything and always taking the unpopular stance. This is untrue. A contrarian puts everything through his own filter and applies his reasoning to determine the validity of an idea.

Many people outsource critical thinking by using convention, analogy, or social proof to filter ideas.

As you exercise doubt and apply your judgement to more situations it will strengthen, like a muscle. The more it fails, the more you course correct ultimately making you less wrong.

Thinking long-term is an integral part of judgement. The whole self-improvement space is just the concept of delayed gratification repeated in various ways. Delayed gratification is choosing the long-term pleasure over the short-term one.

Shortcuts are for losers anyways. Even if you want a quick fix, what you need is a long one.

Think of a rich spoiled kid. One who takes everything for granted, and is a judgmental asshole to everyone. Is their position even enviable?

They were born with it all. Living with their warped idea of the world. They have the lifestyle many strive for, but nothing to be proud of. They can never be self-made or build something without people saying something like “daddy's money”.

All returns in life come from compound interest. Be it in relationships, wealth, or health. The world isn't linear, we live under a power law.

With this in mind:

Even if you are starting from terrible circumstances, no good alternative exists. In chess, no matter how fucked your position is: There is always a best move on the chess board.

Great businessmen and artists all possess a beginner's mind. They have an almost uncanny ability to restart back at zero.

Think of Elon Musk starting SpaceX or Tesla. People told him it'd never work; that he's out of his depth. Now he's the richest man in the world.

You'll see artists who'll make a new album in a completely different style. Their fan base hates it, but they build a new one.

Sometimes the fastest way up the mountain is to go back down the path you spend years pursuing in search of a new path.