career ur doin it rong

Today I learned that I did not get a position at work that seemed perfect for me.
This is the eighth interview I've had at my company without a single offer. My current position is adequate, but provides little chance for advancement and is not where I want to be in five or 10 years.
Why didn't I get the job? The only reason I can discern (aside from any one of several full-blown conspiracy theories) is that I was a bit lighter on technical skills than they wanted, although I was assured during the interview that I would be trained on any technical applications I might need.
It's the ultimate career conundrum--you can't get a job because you don't have experience, but WHERE IN THE HELL ARE YOU SUPPOSED TO GET THE EXPERIENCE? (And I'm a bit old for the Army! Navy! Air Force! Marines! Just the fact that I remember that ad ages me terribly.)
This is a big problem in information technology because the field changes rapidly. I earned a subsequent bachelor's degree in Management Information Sciences in 2002, and what I learned in school already seems dated. I can tell you the difference between ring architecture and bus architecture, but nobody cares. IT job openings make my head spin nowadays. C#? J2EE? WTF?
I haven't done myself many favors. As far as my career goes, I have always had a bad habit of jumping on every bandwagon right before it goes off a cliff. I got into IT back in the good old days, when every other ad on TV was for a dot-com. By the time I graduated, the dot-com boom was gone. Hard to believe that it was only nine years ago that Newsweek ran a cover of a cartoon woman crying and asking, "Why aren't I rich yet?" Now they could have her ask, "Why did I lose my house?"
Also working against me (for most positions) is that my pre-tech experience is in journalism. I once worked for the Daily Racing Form, which makes many techies react as if I'd been in prison. (Seriously, one interviewer actually started to get up from the table when he read that paragraph on my resume.) One person told me that my background had nothing to do with data. Anybody who thinks the Form has nothing to do with data has obviously never read one.
So where does this leave me? Do I keep trying to find another position in my company, hoping that the ninth, 15th, 28th time will be the charm? Do I keep sending resumes out into the black hole of cyberspace?
Or do I just clean up my cube and assume I'm going to be sitting in it for a long time?