All my life, I’ve been surrounded by people trying to look cool. It was probably the worst when I was a teenager, as we all struggled to look cool, be popular, avoid shame, have dates, succeed etc.
For many people, the struggle to look cool didn’t go away when they became adults – even for me, Mr. Perfect (haha). In my 20s and 30s, I wanted to appear like I had everything together – good job, good marriage, good financials, good fitness, good family, good looks and so on. I wanted to be cool.
What changed this for me was hardship. The more things fell apart and I recovered, the less concerned I became with looking cool.
After leaving the best job I ever had (due to ego), I struggled for 10 years of mediocre jobs before rebounding to the level of income and autonomy I had walked away from 10 years earlier. I subsequently went on to have a lucrative and rewarding career. But I never took work for granted again. Nor did I define myself by my job. I worked for money and satisfaction.
Being happily (mostly) married for a long time enabled me to let go of not being the fittest, thinest, best looking man. My wife loved me no matter what I looked like. She had seen me at my best and my worst. Ironically, it was only after she passed away, that I reached my fitness, body composition and health goals. Although this makes me feel good (and feeds my vanity), I doubt anyone else pays any attention to my looks at all.
Attitude, Confidence, Self-Satisfaction – That’s thanks to lot of mistakes, good mentors, people who helped me, a few lucky breaks and taking some difficult actions I know who I am, what I believe, what I value and what is important to me. Hard times built resilience in me that made me who I am today.
Money, Displays of Wealth, Position in Society, Keeping Up With the Joneses – As long as I have enough money to pay the bills and live a frugal life, I’m satisfied. The rest I ignore. I couldn’t care less about how I appear vs. my neighbors, my former colleagues, tech all stars, and the up-and-comers on instagram (or TikTok or wherever).
So am I cool now? I don’t know. It doesn’t matter to me at all.
Juxtaposed to this are some of my friends. Even though they are my age (ancient – aka 40s-50s), they are constantly concerned with looking cool.
It’s sad.
They care too much about their appearance to people who, most likely, barely notice them at all. They drive certain “cool” vehicles. They feign casual behavior when they are deeply emotional about something. They dress in trendy brands, buy status symbol goods and pretend to be worldly, hip or knowledgeable to impress others. They worry about how exes, former and current colleagues, employers, neighbors and acquaintances view them.
They even say to me, “Here’s how I would play it,” as they scheme and plot ways to portray themselves as cool.
My response is always the same,”I don’t play games.”
Then, when they become insistent in trying to convince me their schemes will work I say, “I hope it works out the way you want.” (Actually writing that last sentence makes me feel bad. It’s not honest and it’s petty. I’m not going to say that anymore.)
I met someone recently who is actually cool. I don’t think she even realizes it, which makes her even more cool.
She is self-educated. She has been independent since her teens. She’s self-sufficient. She’s worldly. She has a vocabulary that dwarfs mine and an intellect that matches, if not exceeds, mine.
She introduced to me music I never heard before, she drops words in casual conversation that I’ve only read in literature, she’s quick with a laugh and thoughtful in her responses.
She said she practices radical honesty. (I thought I was the only one).
She lives her life according to her own principles and holds herself to her own strict set of standards.
She’s had her challenges in life. She’s resilient.
Does she drive a luxury car, live in the hot neighborhood, hang out with the popular people, travel to the “right” locations or wear the the latest fashions?
It doesn’t seem to matter to her in the least.
I’v never met anyone like her. To me, she is the epitome of cool.
And she doesn’t even know it.