Sticking the Landing on a Mid-Twenties Career Switch

At some point around age 28, I was ready to call it a day on “success close calls.”

When I was 19 years old, a knee injury that ended my (quite medicocre) basketball career for the local jr. college forced me to decide what was next. At that stage in my life, the only thing I really wanted to do was get into media. WLLR in Davenport, IA gave me a shot from 3–6 am on Sunday mornings, probably due to the fact that I was so eager and nobody else wanted the job. It only took three months of playing Tim McGraw for third shifters and over the road truckers to make my first major career leap. In the fall of 2002, I relocated to suburban Chicago, IL for my first “major market” gig.

Long story short, I thought I was going to be the next Carson Daly or Ryan Seacrest. By the time I turned 25, I’d worked as a host on two nationally syndicated TV shows and had written for more than a dozen magazines. I got a callback to host a show on Much Music (the Canadian version of MTV) but the casting director ultimately went another direction. I had interest in a couple of reality TV show ideas I pitched, along with some initial hits on a gangster movie script I wrote with a friend.

And then…nothing. The second TV show ran it’s course. I never became a Canadian Music Television star, and the reality TV trend started to wane, taking with it my dream of becoming a producer. So that left me with just radio and I was…frustrated and bored. I had no desire to chase a microphone around the country…