Which way do I go?

So, I started out in the newspaper business as a sports writer 10 years ago.
For the last seven years, though, I've been running sideways on a sports desk with no chance of career advancement at a metro in a middled-sized city.
Recently, I've gotten the itch to get back to writing. There's no chance of that at my job now, so I'm wondering, do I take a sports writing gig in some podunk town and work my way up the ladder, or try to get in somewhere relatively the same size.
I think my job on the desk is a path to nowhere, but I'm in solid standing there. At the same time, I'm miserable.
My worries have to do with the ever-present recession and the general shape of newspapers today. But, I think there's a brighter future in writing.
My other option would be to take some Web designing classes and head for the Internet.
I'm at a crossroads ...
Help wanted!

 

Can you do freelance writing on the side while working the desk?

The upshot is that it would give you a chance to get back into writing while you're still keeping a roof over your head. The other thing it will do is give you a chance to add updated clips to your file if you apply for a full-time writing gig elsewhere.

I don't think it'd be practical for you to go take a job at a smaller paper and leave the desk at your current shop. Too many employers might see that as your taking a step down the ladder and wonder about it.

 

While the move downward might be a red flag, consider two things:

1) If you're unhappy at your current shop, then move. No amount of money in the world, in my mind, is worth being unhappy.
2) A simple explanation that the move downward came as the result of it being the only job you could find while moving from the desk back to the writing staff will suffice for most editors.