Cocksure: confident in an excessive or arrogant way.
Skeptical: not easily convinced; having doubts or reservations.
You cannot go through life cocksure of your ideas all the time. You cannot go through life skeptical of your ideas all the time.
How does one resolve this dichotomy?
Being skeptical of your ideas makes you open to change. It forces you to re-evaluate your beliefs. It pushes you to seek disconfirming evidence. It enables you to update your views. In short, it makes you a better decision-maker.
At the same time, you cannot wade through life doubting yourself. You have to execute with conviction. Your execution will suffer if you do not believe in yourself and keep wavering.
How do you execute with conviction while at the same time being skeptical?
I am going to answer this question indirectly by discussing a couple of ideas.
Strong opinions weakly held—is a concept introduced by Paul Saffo. The principle’s gist is to allow your intuition to guide you to a conclusion and then look for information that doesn’t fit or indicators that point in an entirely different direction.
A simple way to think about this is—execute with conviction but keep your mind open to disconfirming evidence and when you find them, update your beliefs; easier said than done.
A great approach to build this kind of mindset is to understand deeply all sides of an idea—not just the side with which you agree.
“I never allow myself to hold an opinion on anything that I don’t know the other side’s argument better than they do.”Charlie Munger
When you believe in something, digesting evidence not supporting your position becomes tough, even when the evidence appears right in front of you. Acclimatizing yourself with all sides(opposite to the one you hold to be true) of an idea helps you recognize and digest disconfirming evidence when it surfaces.
Another way to look at this is not to tie your identity to your beliefs. When you mesh your identity with your beliefs, it becomes tough to be malleable and update your views. The only thing you should be married to is your improvement—if you believe that an idea you held previously is no longer valid, throw it away and update your view.
Even though society does not look favorably on people who change their minds and calls them turncoat, I believe it is a superpower(of course, it does not mean you have to be flippant).
If someone is doing something that is not in line with your beliefs, we look at them with disdain and ignore them. Instead, get curious and keep checking their progress. It is an excellent opportunity for you to learn at someone else’s cost and update your mental model.
You are not going to be right all the time; you are going to be wrong. As long as you are right most of the time and the cost of the wrongs is low, you are on the right path.