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Playing Dumb, Playing It Cool, And Playing To Win: My (Maybe Good) Approach To Dealing With The World

Mitchell Wilson


Mitchell Wilson


Oct 29, 2023

Playing Dumb, Playing It Cool, And Playing To Win: My (Maybe Good) Approach To Dealing With The World

“Act your height.”

Amelia tells me this often. Granted, I am 6’6, but she didn’t mean it literally. I tend to metaphorically shrink myself down around others.

My default is to not take up much space - physically, mentally, emotionally, etc.

I show up to the world like a golf cart, but I'm a fighter jet on the inside I swear.

Playing Dumb

Pretending to be less than I am has its upside.

It’s easier to relate to others, to be more approachable. And people talk way more when you’re a good listener and give them plenty of space to speak. Playing dumb lets you learn a great deal more than you would otherwise if you were bulldozing through a conversation. You get more insights. You get more truths. You get more access.

I’ll give you an example. Immediately after graduating high school I learned that who I called Dad was actually my step-dad, who adopted me when I was 6 months old. That’s an entire story I’ll need to delve into another day, but let me illustrate my point. My mom and I were out to eat a month or two after I learned this and someone walked up to me that knew our family and told me, “you look just like your daddy”. I gave my mom a glance and chose not to correct this woman, but instead be entertained.

This aloofness developed in me as some type of defense, so it has its drawbacks, but I decided a long time ago to make the most of my nature.

Playing It Cool

I’m too humble.

Throughout middle school and high school, my dad would say I needed to come out of my turtleshell, almost on a daily basis, especially in front of his friends and whatnot. Of course, this only made it worse. It was 100% harder to become less shy when this was happening, as you can imagine. And I’m not entirely sure I have ever been ‘without shell’, but what helped was my skydiving job in high school. Finally, a place totally independent of my dad, a place where people didn’t know me at all and I could prove myself with a fresh start. It worked. And I gained a great deal of confidence and ditched a great deal of my shell.

Growing up with a dad who would frequently lose his temp, ingrained in me the complete opposite. The last thing I wanted to do is let anger get the best of me like he would. So I became the chillest dude.

Cool, calm, and collected was the aim.

And (I think) this has served me well. Now, anytime someone is angry, it automatically makes me relaxed. Weird, I know, but that’s how I seem to be wired.

I say all this to say that I’ve perhaps overcorrected in some ways and need to ditch this new, shiny shell game, but playing it cool has brought with it immense benefits for over a decade now.

There are aspects of our nature that can be less of a hindrance if we choose to work with them rather than against them.

Playing To Win

For whatever reason, I just really get off on knowing I’m better than I lead on to be.

But it’s a weird conundrum where I give myself a harder time than anyone else ever will (I’m my biggest critic), yet I’m also my biggest fan with enormous self-belief (my ego is all up in this article as you can tell).

I would much rather people think I’m doing worse than I am instead of the opposite. Imagine the kid in class that you are certain is going to fail the test when all of a sudden the teacher announces he’s got an A+ and the other students are gobsmacked. I’m after that. This is just my nature. Strange? Yes. Strategy? Absolutely.

It’s very much an underdog mindset and I hope this flavor of competitiveness never leaves me.

I want people to think I’m way back there when I’m really well beyond….but who’s keeping score.

“Go big because we all go home.” - Naval Ravikant

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