How to Be Wrong and Overconfident

You Can Do It, Even If It Takes Some Work

I cut my teeth in the finance world for many years. Interestingly (and unsurprisingly), most investors, especially professional investors, believe that they are above average when it comes to investing. Just like 75% of drivers consider themselves above average in driving skills. Both of which are mathematically impossible, since most people (especially 75%) can’t be above average.

But being wrong and overconfident shouldn’t stop us, right? That’s what we’re here for.

So how can we be wrong and overconfident? How can we hone the fine skills of choosing incorrectly while maintaining our misplaced confidence? Our high regard for ourselves and our wrongness?

While many of us have probably been humbled plenty in our professional lives, we can still take certain steps to bolster our overconfidence and ensure that no matter how wrong we are, we can still be more wrong and even more confident about it.

Rely Only on Your Feelings

Data has its place. But how trustworthy is data, really?

What you can trust is your gut. This is especially true in areas where you don’t have years of accumulated, tested experience. That kind of experience muddies the water. It brings too much baggage. Takes too much time.

Malcolm Gladwell, in the book Outliers, discussed the idea that it takes 10 years or 10,000 hours of practice to reach mastery of skills. And those are skills in kind learning environments! As David Epstein wrote in his book Range, learning in wicked environments (where the rules are unclear) is even more problematic:

“In those domains, which involved human behavior and where patterns did not clearly repeat, repetition did not cause learning. Chess, golf, and firefighting are exceptions, not the rule.”

Needless to say, you certainly can’t be expected to spend a decade or more learning and becoming a true expert. What you need to do is look within yourself, feel what is best, push aside those doubts and data to the contrary, and move forward with the confidence of a pilot about to blow up a planet with nothing but magic.

Because that’s what you’ve got—the magic.

Surround Yourself with ‘Yes’ People

A problem I’ve seen with small, young companies is the lack of hierarchy. Problems are too easily grappled with among the teams. Information is easily disseminated and everyone understands what is happening, why it is happening, and how to solve meaningful problems.

In several organizations I’ve worked with, I’ve met regularly with the c-suite, including the CEO, CTO, CPO, CIO, etc. We’ve discussed what’s working and what’s not. This is incredibly problematic because the executives are hearing unfiltered feedback about the good and the bad.

If you want to remain overconfident and wrong, especially as a leader, you can’t be getting unfiltered feedback. You need to ensure that any feedback you get is carefully and meticulously filtered until it becomes unrecognizable and is only what you want to hear.

You need to surround yourself with ‘Yes’ people and create an impenetrable hierarchy.