How-to Hustle

How-to Stop Being So Damn Overconfident

As you approach the bus stop you notice an attractive person scrambling to find their bus pass. The bus is nearly ready to leave. Realizing that if they don’t find that pass soon they likely won’t make it to their destination on time, you offer to pay their fare. The stranger kindly thanks you, and you respond with a resounding —

“So when can I pick you up for dinner?”


Confidence is a commodity that many people can’t often afford themselves. For others, it is dripping from every orifice of their body. At a glance, it may seem like overconfidence always offers an advantage, but in reality, overconfidence can leave us in far more desperate situations than a cringe-worthy failed pick-up attempt.

Confidence vs Cockiness 

Don’t get me wrong, confidence is a very valuable trait, especially among entrepreneurs. But when deployed in abundance, overconfidence can lead to consequences that you may not be prepared for.

If you’ve ever been in a room with me and my close friends for more than an hour, you would know just how argumentative I can be sometimes (a lot of times). This royally pisses some people off, but I enjoy the art of debating and presenting an argument on trivial things.

Sue me.


There is nothing wrong with confidently taking a side in a friendly argument, but there have been times where my unabated overconfidence has lead me to blatant embarrasment. One such occasion happened not too long ago.

Overconfidence Sucks

I spent just over a year working in a massive distribution center. My supervisor picked me and one other guy to help one of the senior employees with a humongous project that involved moving a bunch of product from one area of the warehouse to another, followed by labeling them all appropriately.

The initial stage was straightforward. We moved all of the product in a matter of hours and began working on phase two. This step involved applying specific labels to all of the packages while matching them to several separate categories. As we got started, I confidently told my partner that we could get this done much faster by making a slight change to the process our senior suggested to us.

In my mind, things would get done faster and more efficiently if we went with my plan. My partner attempted to argue that we should just stick to the plan, but I confidently overpowered him, blasting him with overconfidence and misdirected rationalization.

After I’d inflated my confidence to a certain level, I was subconsciously aware of the embarrassment I would face if I backed down. So stupidly, I allowed myself to rationalize a bad plan until it became a good one.

The laws of poetic justice kicked me right in the ass and of course, my plan turned out to be the absolute worst idea ever. We spent several hours peeling labels off of clingy plastic and redistributing them appropriately. I then got chewed out and the next shift had to finish up the job, cleaning up the mess I’d made.

That day was just the worst.

Overcoming Overconfidence

Acknowledge the reality that people are more likely to anchor themselves to the first piece of information presented to them or the idea they came up with first. This bias can create a blind spot that eventually may lead to a dangerous level of false confidence. Consider these mindfulness tips when you are presented with multiple choices and have to confidently choose one without bias.

  1. Consider all options equally
  2. Choose one option to focus on
  3. Assume that this option is the best one
  4. Explain to yourself or other involved parties why this option is valid
  5. Repeat this process for all available options
  6. Select the most valid option

This method is derived from a study done by Ohio State University. It hinges on fact-finding to bolster your confidence in all courses of action, preventing unrealistic levels of confidence in your first guess or whichever option you’ve anchored yourself to.

It also helps to always keep an open ear for criticism and review your failures with an open mind that seeks to learn from past mistakes. Keep in mind that you are your own unique person and you will have unique opinions. The only caveat is validating them within reality.

If you are truly honest with yourself, you should always be confident. But try not to be too cocky or things might go south.

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