Because It’s Cool ?

February 02, 2021

By: Lee LeFever

I write books and run a company called Common Craft. I recently moved from Seattle to a rural island. Here, I write about online business, book publishing, modern home construction, and occasionally, dumb jokes.

I like to think of myself as someone who forms his own opinions. You know, the kind of guy who knows what he likes and doesn’t care what anyone else thinks. 

The older I am, the more I realize that being that person is not natural for me. While I certainly have opinions, I am prone to leaning on the opinions of others or allowing their opinions to become my own. This is especially true if the opinion comes from someone I respect or admire.

I’m not alone. Popular culture is a constant churn of opinions being adopted and discarded, often based on the perspectives of influential people. I’ve always had a keen eye for the churn; what’s in or out; what’s cool right now, or not. It seems like a kind of innate sensitivity I noticed when I was young and choosing to dress a particular way or listen to a specific band. I noticed. I cared, and honestly, I wanted people to know that I cared. 

Lee as a child

For most of my life, I never understood this about myself, or how it impacted me. That all changed when I met Sachi, who does not have the same sensitivity. The churn of pop culture has always been an enigma to her. She tells stories of growing up with friends who made collages from the pages of teen magazines, with boys and bands. They would slide carefully selected photos and stickers into their folders. She had no idea where to start. It wasn’t in her to care and without the sensitivity, she could go through the motions, but not feel it. Unlike me, this perspective meant she was able to form opinions that were authentically her own.

This difference between us eventually bubbled to the surface and has become a subject of ongoing conversation. The discussions we’ve had, could not have happened without bringing something real, yet mostly unspoken, to the surface. Once it came out into the open, it changed how I looked at myself. 

It started with a simple question, asked by Sachi, when I was about to make a commitment, like a purchase: “Why do you like that?” In this context, she’s not questioning my tastes as much as my reasoning. She’s implicitly asking, “Do you truly like this, or do you want to be the kind of person who likes it?” 

This question exposed a reality that I wasn’t prepared to admit to myself. I am sometimes driven not by a sense of objective quality or beauty, but because I think it’s cool and I want to be cool. The real answer to Sachi’s question, more than I want to admit, is “I like it because it’s cool right now.” 

Cool as a Force

Once I realized this about myself, I couldn’t help but see it everywhere I looked. The word is constantly on everyone’s lips. Think about how often you hear “that’s so cool!” My bet is you, too, have considered coolness in making a decision. 

Across cultures and classes, the desire to be cool is everywhere. Yet, it’s mostly unspoken at a personal level. Perhaps it’s difficult to admit that coolness is the goal because trying too hard to be cool is… uncool. I’m obviously painting with a wide brush and I recognize this isn’t everyone’s perspective. But I also believe coolness is a great unspoken force that’s behind more of our decisions than we want to admit.  

Let’s get back to my relationship with Sachi. Once I was able to admit that I was driven by coolness, we both started to pay more attention. The weight of trying to be cool without admitting it was finally lifted and I was liberated. I could talk with her about why I think something is cool, or not. We could explore the idea together and ask: what’s at the heart of this fundamental difference between us? 

What’s interesting about Sachi is that she’s not trying to be cooler than cool. She never decided to ignore pop culture or intentionally go against the trends. I describe it like this: Sachi has zero punk rock. Coolness is just something she can’t see, like a kind of cool color blindness. She has said before that she can’t help me pick new shoes because they “all look alike”. I find that fascinating. 

A few years ago we were about to go out and Sachi asked what shoes she should wear. I said the Chuck Taylors would look good. Sachi then looked at a shelf of shoes which held two different colors of Chuck Taylor shoes and asked me, “Which ones are the Chuck Taylors?” I was astounded and asked her “How in the fuck do you not know which ones are the Chuck Taylors?” She shrugged and chuckled and asked, earnestly “Does everyone know Chuck Taylors?”, “YES” I said emphatically, everyone our age knows Chuck Taylors, but you. Everyone.” Since then, we’ve asked all our friends. Yes, they all know Chuck Taylors. 

Another example is music, which is a continual source of discussion about coolness. Popular music, like pop culture, constantly churns and one of my favorite pastimes is exploring and discovering a new sound. Part of the process is knowing what influential people think is cool. For Sachi, it just doesn’t compute. She has zero interest in adopting new music because other people think it’s cool (except perhaps me, and that’s a struggle). So, she sticks to oldies and I play albums over and over to condition her into liking them. 

While she can’t see shoes or music in the context of coolness, she has an amazing eye for home design and finishes. She can thoughtfully critique music, poetry, and economic trends. Yet, when it comes to making a personal choice related to current fashion, or what others might think is cool, she feels flummoxed and always has. She’s spent her life feeling frustrated by these decisions and for many years, I thought I could help develop her sense of style, but came up empty. It’s bigger than that. I now feel it’s like trying to teach a blind person to see. 

This SNL skit is the closest thing I’ve seen to capturing Sachi’s experience with clothes.   

What’s the Point Here?

I don’t have a big thesis. I am just fascinated by human nature and believe that we’re all more different than we realize. We all have blindnesses and sensitivities that make us who we are. And often, these are not things we can control or even recognize about ourselves.

What Sachi and I found is a way to bring the differences to the surface so they can be inspected and analyzed. It was a revelation to admit to Sachi (and myself) that I’m driven by what’s cool, even if the admission itself is uncool. Discussing Sachi’s blindness to coolness helped explain a lifetime of insecurities about clothes and fashion. We are very different people and by understanding the differences, we can find the best ways to work together. 

We’re not unique. Blindnesses and sensitivities help us all interpret reality, even if we don’t realize it. If we look just below the surface, we might find parts of ourselves that we never noticed before. They may seem embarrassing to admit, or unreasonable, and that’s fine. The key is understanding that they’re a part of us that may not change. Instead of fighting against them, consider how to use them to your advantage.


  1. mathemagenic

    I think I am a bit like Sachi when it comes to “cool”. I only find it an issue in a society where there is an expectation to be “cool”, to adhere to what is in fashion or trends, to be aware of a social pressure and to let it influence your choices. Yes, knowing what is “cool” is useful when you need to fit in or get accepted on a bigger scale than you would be otherwise, but it is often comes at a price of knowing your own preferences and being able to go for them regardless of their “coolness”.

    As for the clothes, given fast fashion being blind to what is “cool” might be a way to go – shopping in thrift shops gives much bigger choice than what recent collections, is more sustainable and can lead to development of a recognisable personal style that is never out of fashion.

    • Lee LeFever

      Thanks Lilia! I love seeing you comment here. I remember seeing your name in comments many years ago! Welcome back! I agree about fast fashion. That’s been one of the changes for us living on the island. There isn’t much of a reason to buy nice clothes. We prioritize comfort and durability.

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