Expanding My Repertoire

Now that I've gotten the hang of writing for VerbNews I've decided it's time to continue my search for publication. Just because I have one job doesn't mean I shouldn't be on the search for another. After all, if I ever hope to make my living solely from writing, it definitely won't be with just one gig. VerbNews is great, they gave me the opportunity to get my foot in the door, gain experience and build up a few clips, but I won't be happy with just that.
I've decided to start small. I'm reaching out to all the small, local papers and publications, hoping to catch my second break. If/when I do, then I will learn all I can from them and continue expanding. Next will be more provincial publications, followed hopefully by national ones. I'd love to nail down a job blogging or writing a column. My favourite is the personal essay (aside from novel writing of course), and if I can find a few publications that like one or two enough to print them I'd be in heaven.
It's always a little intimidating plotting out an e-mail, reaching out to people, knowing that rejection is a major part of the game, but it's better than plateauing. I don't want to get too comfortable. Success requires constant drive and a never give up attitude. To be incredibly lame, I have to be like the little engine that could. Do you remember that story? "'I think I can, I think I can, I think I can...'" It's silly but it's true. With all the rejection, writing can sometimes feel like you're trying to ice skate up hill. Why bother? But I have to bother, I have no other options. The only back up I have is working a dead end job and I really don't like that back up.