“When is a person no longer interested in being cool?” That was the question asked at a business meeting I attended this week. As you know, I’ve been doing a little soul searching and research on that very topic here in this column so I was naturally interested. For some context—as you may know I work in radio. Don’t let the fact that it’s an all news radio station on the AM portion of the dial fool you: it’s still radio. Part of our job is to keep up with the current trends of how media is being delivered and what one generation is using that a previous generation didn’t. The question was part of a larger topic about Facebook, Pandora, Foursquare, etc. and the generational difference in our feelings toward this media. For instance, I have no problem using GPS related devices but other people in the office (older than me) have a big problem with that. So, as part of that we were discussing if a person used some of these devices, programs and apps to feel cool and be part of the group? Answers surprised me.

For the most part the answer was at the age of 40. The answer weighed heavy in the air for me. My first thought was I’m not 40 so there’s still a chance. Still a chance? Still a chance to be cool?! I’ve never felt uncool, at least among my peers. I know that kids don’t see me as cool but I think most of my generation does. They have to, it’s what I take solace and refuge in. No, it’s not a chance to be cool. Instead I think it’s to have an impact in a field that’s considered cool. Stay with me because I know it doesn’t seem like much but I think to a lot of people like myself, it just might mean close to everything.

As I’ve documented previously in this column, my intent was to be an artist. I’ve done several things, sometimes combining several different mediums but the two main ones have always been writing and music. Writing is kinder. You can take as long as you want to write the next great American novel. No one will think you less hip for doing it in your 40’s. Let’s be honest though, the chances of that happening get slimmer with each passing year. While you can write the next great American novel when you’re 42 those are usually written by people in their 20’s—take a look at some of the previous great American novel writers—Hemmingway, Fitzgerald, Kerouac, Coupland, Gibson…all in their twenties. Oh sure, there are stories of housewives slightly past their prime partying years churning out megahits about sorcerer boys or vampire teenagers but those are the exception. Music is nowhere near as kind. By the time you’re 32 if you haven’t made it you aren’t going to make it, which means it becomes a hobby.

So here I am getting ready to celebrate my 39th birthday in about three weeks. Where does that leave me? Have I lost the ability to do something cool? If I do create something cool will it matter? I’m sure these thoughts are completely foreign to many of you who may be reading this. I mean no offense but I know that the lawyers, doctors, engineers probably didn’t ever think they were going to create anything cool, never had dreams of being anything beyond their careers. My friends though, the people I know, we still dream about it. The thing is though, I can feel it slipping away.

The way I look at it, the real world Dave is slowly surpassing the artsy Dave. Every morning that I wake up and put on a tie and a sports coat I’m slowly choking the artsy Dave, every practical decision I make is another tear in the fabric of the art-space-time-continuum. There’s a great quote in the movie Singles. One of the characters says “somewhere around 25 bizarre becomes immature.” When I was 24 and the production director a radio station having jet black hair in a goth cut was cool, now that I’m almost 39 not so much. I see it when I show up at event at my son’s school and I’m wearing a Betty Page or Led Zeppelin t-shirt. It’s now immature. It’s immature to not want to have a perfectly manicured lawn but to long for a published poetry collection; it’s immature to spend my time playing guitar rather than getting to know craft beers; it’s immature to believe that time might still offer me the opportunity to make an impression that will last. As David Lee Roth might say, “funny, I don’t feel immature.”

I’m not sure we’ve ended this column where we began. My original intent was to write something a little lighter than the past few weeks and discuss the theme of coolness. Not sure that’s what I did. It may seem like I feel it’s a dark place turning 39 and not having written the great American novel or this generation’s “Stairway to Heaven” but it’s not. I play in a band on the weekends, write a weekly column and still have a few ideas for poetry and novels. I may not look as hip as I once did, at least Monday through Friday from 8 AM to 5 PM (I still look pretty damn awesome on the weekends!), but I still feel it. I may still have a few years left of coolness. Here’s the cool thing about spending close to 21 years trying to impart my hipness on the world—I have some great stories to tell, they may yet weave the threads of the next great American novel.

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