Getting Over Confidence: Why Self-Assuredness is Highly Overrated


I well remember while going public, when my executives and I were supposed to pitch in front of our investors.   Our Investment bankers helped us prepare the slides. We divided the presentation amongst us. In the initial practice we were all gagging with nervousness.  We could not believe what was happening to us.  We were proficient in making polished presentations to our major customers, but here, we needed to pitch the company and ourselves, and not our products.  We had no practice and did not know how the investors think.  That nervous tension was reflected in our humility, and our bankers and investors liked us. I would not say we had a polished IPO road tour. We were never sure we were doing it right. We were not confident. But we had a successful IPO. 

Overconfidence is the opposite mental state of what entrepreneurs need to maintain to succeed. Humility, alert curiosity, and a thirst for new knowledge are far more important than confidence (even critical). To be overconfident is to shut down. What is the point of paying attention? What is the point of thinking deeply about any subject? We think we already have all the answers. The same applies to other people. If you are overconfident, you have little or no interest in listening closely to what others are telling you. If you believe you have nothing to learn from them, then you will learn nothing. 

A conversation is dull and boring any time an overconfident person is present. Such people believe their role is to tell others what to do. Who wants to have that conversation? In a business setting, you want to hire people who are listeners—and you want to work for people who are listeners. 


When venture capitalists look to fund a startup, they look for conviction—for confidence. If you ask me, I would say that confidence is overrated. Entrepreneurs do not need confidence to succeed, nor should they be told that they must be confident. Overemphasizing confidence pushes us in a direction that plays to cognitive weaknesses that can blind us to reality. And worse. I’d say don’t use confidence. Use logic and try to use your own brain to work, not your ego.

The Nobel-Prize-winner Daniel Kahneman in his seminal book Thinking, Fast and Slow. explained that confidence must be tempered with cognitive biases to be useful.  Our brains are designed to predict the future based on simple rules of thumb that poorly capture the complex realities of modern business and life. 

Ours is a prediction machine that is optimized for a different way of living, out in the wild, before cities and technology. So, believing and following our natural reaction — our confidence — blindly is a form of misplaced confidence. In fact, every entrepreneur I have spoken with in candor has told me they were always doubts, they were never sure about anything. The good ones used logic to overcome doubts, not confidence.

Some startup experts says you have to have confidence to succeed as a founder. I do not subscribe to the notion that if you have confidence then better things happen. Better things happen when you make smarter decisions and with some luck. If confidence is a feeling you get after making progress, a feeling that energizes you, that is surely a good thing. But is it correlation or cause?

Far from being necessary, confidence can often be a liability, or at least an overabundance of what people call confidence. As the Indian writer Sadhguru said, “Confidence and stupidity are a very dangerous combination, but they generally go together.”

Overconfidence is the opposite of what we need to maintain, which is an alert curiosity, even a thirst for new knowledge. To be overconfident is to shut down. What is the point of paying attention? What is the point of thinking deeply about any subject? We think we already have all the answers. 

The same applies to other people. If you are overconfident, you have little or no interest in listening closely to what others are telling you. If you believe you have nothing to learn from them, then you will learn nothing. Conversation is dull and boring any time an overconfident person is present. Such people believe their role is to tell others what to do. Who wants to have that conversation? In a business setting, you want to hire people who are listeners—and you want to work for people who are listeners. 


The one sense in which the word “confidence” works for me is when it is used in the sense of quiet determination, as when former U.S. First Lady Eleanor Roosevelt, a woman ahead of her time talked about confidence as a destination on the far slope of fear. “The encouraging thing is that every time you meet a situation, though you may think at the time it is an impossibility and you go through the tortures of the damned, once you have met it and lived through it you find that forever after you are freer than you ever were before,” she wrote in her book You Learn by Living.

In my years building a company from a two-person team to an IPO on NASDAQ, I was not once sure of any major decision. I always knew I might be wrong. And I saw curiosity and humility as dual allies that can help fight off overconfidence. I always sought to talk to people who didn’t agree with me and listen to their views. And not once did I assume that my success was inevitable or even likely. I was always, always a little bit afraid. But I learned how to use my brain to overcome the hard-wired tendencies and put the unhelpful voices of ego that lead to overconfidence in their rightful place — as bystanders in a decision-making process.

Confidence is great. I am happy for people who believe in themselves. And an excessive lack of confidence can be paralyzing. That is for another column. In my case, I grew over time more and more to trust and believe in myself. But never completely. Even today, I lack confidence and that’s a good thing. It is not to the degree that I am paralyzed or even prevented from trying new things. But my lack of confidence fosters humility and curiosity. It empowers me to ask those who have more experience or who have interesting ideas what they think and do so with genuine interest.

Along the way, even as I heard people prattle on about the importance of confidence, I noticed something funny.  The people I admire the most arrive at confidence after pursuing logic and — this is perhaps the most important part — they tend to keep their confidence to themselves. I am over confidence and always on guard against it. You should be too.