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I used to put a lot of energy into making my Facebook profile look cool. I would make sure my photos were all funny and/or artsy, my status updates clever and my ‘favourite music’ reasonably obscure.

It wasn’t just my online persona that I edited. I also tried hard to befriend the kids in the arts scene and at the dance parties.

Where did all of this get me? Yes, people started asking me for music advice. I had a fun summer dj’ing at a local bar with my buddy (we called our night ‘Touch Me Tuesdays’, it was epic). I was also definitely the big cool fish when it came to the small law school pond (not hard to do).

But did I become close with the kids in the scene? Not really. Most of them weren’t all that nice and/or interesting. Did my social life take off? Not especially. Did I have more fun? Actually I found most of those dance parties rather stressful, constantly worrying about who was there or what kind of drama was going on that month.

The truth is that for the most part, trying to be cool made me really unhappy.

The New Social Hierarchy

I don’t want to go into some anti-hipster rant like that horrible adbusters article. That’s not what this is. But I do have a theory about where this desire to be at the center of the scene comes from.

In high school you’ve got the in-crowd, right? Everyone wants to be like them, dress like them, and so on. Well now that that’s over and we’ve gone out into the world, we know how artificial that hierarchy was.

Over the last eight years or so, this awesome culture based around art and digital democratization has evolved- amazing music, creativity, activism, vintage clothes, all great. Suddenly, the people who were not a part of the in-crowd when they were younger have a chance. They have a chance to be at the top of this new social hierarchy.

However, this new hierarchy possesses the same traits as the old one. There’s a central group of trendsetters that everyone wants to be like. People dress like them, try to befriend them and put way too much effort into customizing their facebook profiles to appeal to them…

Coolness is About Comparison

If coolness were used as a stand alone term, there would be no problem. In fact, these days when I refer to someone as ‘cool’, what I generally mean is that this is a person who knows who they are, embraces who they are, puts themself out there and is unapologetic about it (and usually it’s a person who’s really fun as well). In this context, coolness isn’t such a bad thing.

Unfortunately, however, the word cool is often used in a comparative context, as in “this person is cooLER than…” Even if it’s not said out loud, it’s usually implicit. And therein lies the problem.

Trying to be cool is typically a process of working your way up through the social ladder and assessing your progress by comparing yourself to (and judging) others.

Judging Others Hurts Only You

I don’t think people realize how true this statement is. Every time you think something negative about another person or compare yourself to them, you are hurting yourself. Every time you ignore someone or withhold affection in order to gain social value, you are hurting yourself.

It might not feel like it at the time because thinking “I’m cooler than them” does provide you with a sort of instant confidence boost. But in the long run, it’s yourself that you’re hurting.

See, whatever you focus on is what your mind perceives as important. Putting your energy into being cool is like training your mind to derive its validation solely through comparison to others. This doesn’t feel good. It makes you worry constantly about whether you’re measuring up and whether others are judging you. It makes you feel competitive and defensive.

Loosing Your Individuality

The drive to be cool makes you loose sight of your individuality. When your ideals don’t match up with the groups’ ideals, guess what happens? Your ideals change.

Missing Out on Awesome Friendships

Trying to be cool can lead you to miss out on knowing a whole lot of amazing people simply because you’ve already disqualified them. For instance, I know people who only surround themselves with others who are exactly like them. I just think about how many incredible friendships I would have missed out on had I gone that route.

The Relationship Between Coolness and Confidence

It’s not only ‘hipsters’ who judge others. Many many people do it. It’s actually quite rampant in our culture and it’s because most people are looking for external validation instead of providing it for themselves.

One of the traits of truly confident people is that instead of deriving their value from being better than other people, they derive it from helping others and making them feel good. They know inside how awesome they are and don’t need to be constantly proving it to themselves by striving to be cool.

Instead of Being Cool, Try Featuring the Things that Make You Unique

It’s important to put yourself out there and be unapologetic for who you are. You can’t do that if you’re constantly trying to be cool. Would I have started Puttylike if I were trying to be cool? No way! I would have been terribly afraid of being judged. Starting personal development websites is not exactly hip.

In fact, trying to be cool is fundamentally incompatible with pursuing your dreams. So if you want to build a life that integrates your many passions, you’d better stop worrying so much about what others think.

Judging Others is a Sign that Something’s Wrong

I’m pretty happy to say that I’ve reached a point at which I hardly strive to be cool at all. I just try to be myself. In fact, on those days when I notice myself comparing myself to others, it’s a good sign that something’s wrong- that I’m feeling insecure or worried that day. That’s usually when I check in with myself to see what’s up. I also stop the judgmental thoughts instantly because I know they will only make me feel worse.

I no longer worry about wearing the right clothes or befriending the right people. I just do what I want to do and I’ll tell you, I’m much much happier. Everything in my life is better.

Finally, when I add or subtract something from my Facebook profile I now think, am I doing this because it’s who I am or am I doing it to look cool? That usually tells me what I need to know.

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What do you think? Have you observed yourself trying to be cool or comparing yourself to others? How have you dealt with it?