I went to college with the intention of making my living in radio.
Money well spent.
I guess it wasn't that big a pipe dream, but it wasn't all that realistic, either. Maybe if I'd been willing to be the kind of person that moves all over the country every year, making meager change in small markets and DJing clubs on the weekends to supplement my income. But I didn't want to be an absentee father. And I figured the Boston area had enough radio stations. And with Providence nearby, that should have expanded my options.
But man, schools churn out aspiring Howard Sterns by the truckload. Nobody told me that beforehand. And those folks will fight you to the death for the crappiest paying gigs. Add to that the egos and the outright scumbags in the business, and a guy who's not too into confrontation and tends to retreat into himself doesn't really stand much of a chance.
Nevertheless, I stuck it out for a few years, mostly because it really was a fun job. Whether I was on-air or producing, I got to hang out with some pretty incredible people, meet a lot of folks who've influenced me over the years, and go to see bands and comics and other events that I'd never be able to afford to do. Yeah, guest lists were a huge side benefit. Also books. Turns out, if you work in radio (and TV and other media, of course), you can call a publisher and get a review copy of pretty much any book out there. Pretty sweet for a guy who likes to read.
Unfortunately, the reality of low income and the decreasing likelihood that it would get any better made me make the painful decision to give it up. Besides, I'd gotten into standup at that point, so my creative jones was satisfied. I still miss it sometimes, but in the 12 years since I left, opportunities have gotten only scarcer. More and more stations are going DJ-less, and the talk radio side, for the most part, is populated with people I wouldn't cross the street to piss on. So no, I don't regret not being in radio anymore.
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