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Wow. Good question. Two answers.
If I woke up and was 18 again and it was 1968 (when I hit 18 the first time) I’d probably do what I did!
I wanted to be on the radio from the time I was a little kid. I pursued it. It was nearly everything I wanted and expected. I wish my radio career would have gone farther. I left before the era of the high concept/big deal morning show. No regrets.
In fact I have few career regrets except for signing with and depending on an agent to advance my career. In my opinion he, a very well known agent, did nothing for me. Not that he didn’t get me a better job–he just did nothing while taking a significant slice of my gross! Someone I work with has the same experience with the same guy. I pissed away years waiting.
Time seems infinite when you’re 18. It is not.
If I woke up 18 and it was today I’d actually finish college and try to vertically develop for the web. I understand how both the computer side and content side work which still seems to be rare (Leo Laporte and Kevin Rose being two notable exceptions). I am not against wearing many hats. Creative work is satisfying work to me.
The future of ad supported web content is narrowcasting–sort of the opposite of what I currently do. I’d probably still be in front of a camera, but on the web, not TV and well known to a small subset of society who had some affinity to each other.