“In an age of nearly infinite leverage, judgment is the decisive skill.”

As I mentioned in last week’s post on the value of getting exposure to topics outside one’s area of expertise, the issue of sharpening one’s thinking has been top of mind recently.

Maybe it’s my default mode network simply doing its job, but I constantly find myself wondering whether I chose to work on the right projects, whether I should have organized my daily schedule differently, and which misconceptions lie in my understanding of this or that topic.

Why spend so much time at the edge of paranoia against my own mind, always wondering how you could be wrong and what you could do better?

Because, as Naval Ravikant succinctly puts it, in an age of nearly infinite leverage, judgment is the decisive skill.

We live at a time where anyone with access to the internet, an idea, and time to work on it can generate value in the world and be rewarded for it. More and more people are becoming scalable, and generative AIs are compressing how long it takes to get started on creative projects.

Notice that the rewards are not necessarily, or only, monetary. One could leverage their skills to find work in a remote, async-first, result-oriented organization and, in return, gain lots of control over their schedule. Time affluence is as valuable as money affluence.

Great rewards await those who can best leverage their skills and ideas. This is why knowing which lever to push on is paramount.

So, How does one go about improving one’s judgment? This is where things get tough.

Naval defines judgment as “knowing the long term consequences of your actions and then making the right decision to capitalize on that.” He also explains that good judgment is hard to acquire because it requires intellect and experience. You need both theory and practice.

To someone like me, the theory comes easy. I’ll happily spend hours reading books, thinking about them, and trying to find connections. But, as Naval points out, experience is even more critical.

10,000 tries are better than 10,000 hours. But it takes more than simply trying 10,000 times. Each iteration needs to inform the next. You should have some sort of accountability system, skin in the game, to clearly differentiate between failures and successes.

In short, improving judgment takes time, effort, and intention. It’s an ambiguous process that inevitably results in making mistakes along the way. If it sounds hard, it’s because it is.

The barrier to entry has never been lower, and the ceiling has never been higher. It’s only fitting, then, that judgment, the crucial skill that makes all the difference, should be hard to acquire.