Quick Takes:

  • The definition of “cool” has become one based on external factors
  • What it means to be cool is dynamic and changes over time
  • Our personal definition of cool should become deeper and more complex over time
  • Rather than looking externally, look internally for your definition of cool
  • Use that understanding of cool to create lasting change

Why is it that our perception of “cool” changes over time? Sure, the Legos you had as a kid aren’t quite as cool as the luxury car you have now (although I might argue otherwise), but it has to go deeper than that.

Your perception of cool doesn’t solely change with age, and it doesn’t even solely change with your evolving tastes; by and large, your perception of cool changes based on your level of achievement.  

If you think about it, once you get into the “real world” (not quite sure what the real world is, but I’d rather not live there), your definition of cool changes from toys and high school popularity, to one based on goal achievement and the status gained through that achievement.

What do you think is cool now? Probably the title of a job, the job itself, the things you’re able to buy as a direct result of that job, or the combined trajectory of it all. Am I wrong?

So, if our current definition of cool is synonymous with our life’s trajectory, then its natural that our definition of cool will be as dynamic as that trajectory, right?

When I was a debt-laden graduate of San Diego State, for example, I remember thinking that becoming a Financial Analyst would be so cool – the coolest even. Back then, I was still deriving the value of my life from external factors, and I was enamored with the idea of introducing myself as a Financial Analyst. So lame, I know.

I couldn’t even have told you the difference between a corporate Financial Analyst vs an investment Financial Analyst, but I knew I wanted to be one. So, I became one! A Financial Analyst, that is. And it was cool, for a brief moment in time, but I it didn’t really resonate with a higher purpose, and the allure quickly faded.

Still romanticizing the financial path I was on, I figured the feeling of cool had warn off because I needed more responsibility and needed to get in with a startup. Startups are cool, right?

So, I did that too. I became the Director of Finance for a VC-funded startup, and, let me tell you, I felt pretty cool. But again, I was deriving the feeling of cool from an external source. It was the title on the business card I thought was cool, and the feeling of responsibility that came with it.

Over time, and through a few arduous years of self-improvement and mindset shifts (haven’t finished yet, I’ll let you know if that ever happens), I began to understand that cool is an ownership of your emotions, time, and location, and not based on external factors like titles and status. Owning your own location-independent business, then, would be pretty cool.

Which makes me laugh, when I look back on how enamored I was with the idea of being a Financial Analyst. That life-path doesn’t even fit in with my system of beliefs anymore. If I was still a corporate drone I would feel very much un-cool. But, at the time, that’s all I could imagine doing.

Never again. 

And although we reach present day in my journey, I can already feel the next evolution of my cool. Entrepreneurship is pretty cool, but I now wrestle with the idea of legacy. I sense that the next level of cool is to parlay our abilities into a something that has a positive social impact. For me, that means starting a business that leaves a legacy. Freedom and location-independence is cool, but leaving a legacy is so cool it errs on the coolest…I think, for now.

What does my journey highlight about the idea of cool?

It puts weight on the value of the process over the achievement. Basically, its natural for us to tie our identity to some sort of goal, and when we reach that goal, it’s kinda, well…hollow.

For a brief moment in time it feels great. But the satisfaction you get from achieving a goal decreases exponentially as time passes. I often find myself, even immediately after achieving a goal or a certain “level of cool,” asking “ok, well what’s next?”

Point being is that a lot of things seem cool from the outside looking in. Then, once you get on the inside, you realize that it wasn’t quite what you expected. Which is why it’s so important to place higher value on the process.

I always think back to aspiring entrepreneurs. If you were a new entrepreneur who recently quit your job, and you told someone that you were an entrepreneur, they would be extremely impressed. They would associate their romantic idea of what it means to be an entrepreneur with you.

But, unknown to them, chances are you’re barely scrapping by as you’re trying to plug the many leaks in your sales pipeline. You’re probably living in a heightened state of stress as you try to get your company off the ground.

To you, you probably don’t feel very cool. In fact, you could be feeling like a failure. But to the outsider, you’re the coolest.

So then, what is cool, and how should we define it?

To me, cool is the active pursuit of of a higher calling that results in self-growth otherwise impossible. Cool isn’t a title or a thing, it’s a state of mind. Your idea of cool evolves, not because of your life trajectory per se, but because though the active pursuit of cool, you strengthen your positive mind and deepen your understanding of life. Your surface level idea of cool will give way to more complex understandings of what it means to be cool, and how exactly to achieve it.

So, by this logic, it’s much better to be someone living paycheck to paycheck and loving life, than a hedge fund manager who makes millions and dislikes what he does.

With the traditional definition of cool, the hedge fund manager would be the coolest, but we now know that cool is a state of mind, and as long as you’re happy and comfortable with yourself, both where you are and where you’re going, you’re pretty cool.