When I started this project, I honestly never believed I might win anything. Yes, I dreamed about winning the National Egg Toss Championship, and I thought I had a great chance of winning the Big Boss Potato Decorating Contest. But I never really believed those dreams might come true. They were just dreams.

Even when I recently decided to start entering random online contests, my pessimism was abundant. I’ve been entering drawings and sweepstakes all my life, with nothing to show for it. I’ve never won a door prize at a company Christmas party. Never had my business card picked from the fish bowl for a free meal at my favorite lunch spot. Since blind luck had never been on my side, I figured, I might only win something on pure determination and grit.

But my luck is finally looking up. Today, anyone can win. Even me.

Last month, I entered Colorado artist Pam Boutilier’s online contest. Each month, Boutiler is awarding one lucky winner a free 5″x7″ ink painting of his or her pet. The rules are simple. Simply submit a picture of your pet and drop Pam a line about why your pet should win.

I chose a picture of our eldest mutt, Bailey, that I took a few years ago while living in Athens, Ga. Here’s what I wrote to Pam when entering her contest:

Attached is a picture of my dog Bailey. He’d been at the pound in Athens, Ga., for 2 weeks and was next on the kill list when we rescued him. My wife and I are convinced that he is a person trapped inside of a pup’s body. In addition to his many outstanding qualities, such as destroying couches, we love his most obvious physical characteristic: his right-ear-up, left-ear-down combination.

Pam soon responded to tell me that Bailey is a gorgeous pup and that she would notify the winner by the last day of the month.

For the next two weeks, I barely thought about the contest. Then, this morning, wedged in my inbox between a special offer from The Onion Store and a notification from Netflix, there it was. An e-mail from Pam. Right there in the first sentence were the words I could previously only dream of reading: “You won!”

Pam’s husband literally picked my name from a hat, and Pam has already completed Bailey’s portrait. Not only that, she did a fantastic job! See for yourself in the image below. You can also check out Pam’s post here: http://catinaboxstudio.blogspot.com/2010/06/desktopper-contest-winner.html)

(Doesn’t he look regal in painting form?)

Had you asked me before this victory, I might have told you that I would retire from Anyone Can Enter if I ever won something. Go out on top of the mountain, with some of my dignity in tact, like a graceful legend.

But the taste of victory is far too sweet. Like a drug. It’s so addictive, I can finally understand why Michael Jordan made two comebacks to basketball. Why watch from your La-Z-Boy as somebody else wins it all when you know the only thing standing between you and them is a little bit of rust? I hear ya’, Mike. I hear ya’. Makes total sense now.

So, rather than calling this thing quits, I’m just getting started. By this time next year, maybe I’ll even have a trophy room to rival Sue Sylvester. Whether I actually believe that or not, it’s certainly worth dreaming about.