You don’t become cooler with age, but you do care progressively less about being cool, which is the only true way to actually be cool. Call it the geezers paradox.

-Author Unknown

I’m 53. Not quite a geezer, but I can see my geezerdom from here. And now I do care less than in my youth about being cool, which the Geezer’s Paradox notes as being cool. The idea that thinking about being cool is uncool seems spot on. It’s similar to the notion that Mark Manson expresses in his fantastic essay “The Subtle Art of Not Giving a F*ck that life is better if we are choosy about what f*cks we give. (I wish I could inject some of this into young people who live their lives so that it looks good on social media.)

Speaking of whether caring about being cool makes us uncool, you might find the email exchange I had after buying a new pair of skis way back in 2019 entertaining. The skis are “Masterblasters” from J Skis, below is a picture of them (top and bottom) — pretty cool, right? Yes, the graphics on the tops of the skis are things you need when you go camping (why not?).

Shortly after buying the skis, I sent the following email to Jason Levinthal, the founder and CEO of J Skis (and he’s the ski designer who invented twin-tip skis).

Me to Jason:

I am super excited to ski on my new Masterblasters this year!

I am somewhat concerned they are too cool for me.

Thus, I am confronted by the following paradox: Should I try to be more cool to live up to these skis? But by doing so, I’ll become, by definition, less cool. In fact, even thinking about coolness makes me uncool. 

So, I think I’ll just not worry about it and let the skis and skiing speak for themselves.

I didn’t expect buying new skis to launch me into an existential crisis. LOL.

His response:

Haaaaaaaaa that’s hilarious and I can assure you, these skis will do 2 things…

1) make you look cool

2) not make you look like you’re trying to look cool

NOTE: No guarantees on actually becoming cool, sorry

Please try to just enjoy the new high fives coming from people you don’t know in the lift line and on the chair!

BTW – my Masterblasters are the best skis I’ve ever skied on.

Have a nice Labor Day weekend! Go forth and not care whether you are cool!