The Geezer’s Paradox: Why Trying Too Hard to Be Cool is Killing Your Sports Marketing Game

My kids remind me daily that I’m not getting cooler with age. And honestly? I’m okay with it.

I saw this meme the other day that stopped me mid-scroll: “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. The geezer’s paradox.”

It got me thinking about how much time I wasted earlier in my career trying to be “cool” in my work—chasing trends, over-designing, and overcomplicating messaging to impress clients. Sound familiar?

Here’s the thing: In sports marketing and media, the pressure to be cutting-edge is relentless. But what if the secret to standing out isn’t about being the flashiest or the loudest? What if it’s about being authentic?

I’ve learned that the most magnetic brands and professionals aren’t the ones trying to prove they’re cool—they’re the ones who focus on solving real problems, telling real stories, and connecting on a human level.

So, here’s my challenge to you: Stop trying to be cool. Start being confident. Simplify your message. Market with purpose. And most importantly, care less about what others think and more about the value you’re delivering.

The result? You’ll not only attract the right clients—you’ll become the kind of partner they can’t imagine working without.

Let’s embrace the geezer’s paradox together. Cool is overrated. Impact is forever.

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