June 22nd, 2020
In high school, I was not cool.

I came from a small town, with a graduating class of about 150 - the kind of high school where everyone knows everyone - the type of high school you’d see in a Hollywood movie.

However, I was not the type of uncool where I was secretly cool.

I was just the type that was uncool where I secretly wanted to be cool and popular.

I probably wouldn’t have admitted this at the time, but it’s so obvious now.

I can remember all of the popular kid’s names right now - Adam Stanton, Alex Salazar, Sam Cooper, Mitch Van Dyke, etc.

Those guys were so cool, and funny. I wanted to be them.

I probably had a bunch of opportunities to be cool in high school, but I ruined all of them, probably from trying too hard and caring what people thought about me.

After high school, I still wanted to be cool.

In college, you get to start over. And that’s what I did.

I went to a college thousands of miles away, and I worked hard to be cool.

I was more successful at this in college - and I actually became somewhat of a ‘cool kid’ - at least in the eyes of the previous popular kids I wanted to impress so bad in high school.

A couple of these guys from my high school visited me at college. We hung out and became a sort of friends. Nothing crazy, but all of a sudden we were chilling like some normal dudes. I think they thought I was cool.

Yet, in college, I suffered the same problem. 

Once I leveled up my cool factor, there was now a cooler group of kids - and I wanted to be like them.

Just like in high school, I wondered what it would be like to be these cool kids.

So I did the same thing - I worked hard to get to their level. 

Then I got there.

You can probably guess where this is going.

The cycle continued. After college, I discovered the next batch of cool kids. But this time it was about the cool job and the cool career.


I don’t think this mentality is all that healthy - but I also think that it’s a part of what drives many successful people and high achievers.

Becoming cool did not solve my problems - but it did get me closer to what I was really looking for.

When I chased the approval of others, I eventually got it - and it was always at that point where I realized it was never what I wanted in the first place.

This is my story - I did this enough times that I've trained my brain to care less about being cool.

These days, I live in my parents' basement, own just a suitcase of clothes, I'm not in a serious relationship, and run an online business from my laptop. 

To 99% of the world, this is extremely uncool.

Sometimes people will tease me about this, but these days I just laugh it off. It doesn’t bother me as it would have five years ago. I secretly know I'm cool as fuck - but I don't need to show it.

Maybe this is just me again trying to be cool... but it feels different this time.


About a year ago, the #1 cool kid from my high school sent me a message telling me how he was inspired by my story.

We got to talking, and I told him how much I had admired this speech he did back in high school. Here was his response:

"Honestly my motivations for that speech came from my own struggles with fitting in and going along with norms and my experience of being judged by others for the smallest, dumbest, and meanest things."

It just goes to show you that all of this shit is just in our heads.