Feeling lucky?: Contests and Sweepstakes

I've loved contests and sweepstakes ever since I was a little girl. Going with my hunter-gatherer analogy, I consider it hunting for exotic treasure - you don't really expect to get it, but when it comes in, it's a delight. Blessed with good luck (and a healthy dose of superstition - I'm knocking on wood right now), I've won lots of things, including tickets and backstage passes to a B-52s concert, several pairs of tickets to Yanni concerts (I never went to any of the shows), cases of soda, and several years supplies of Schick razors.

The chances of winning are often minuscule, so here are my guidelines for entering contests:
1) Only enter if it is a joyful process. I've gone through obsessive periods of entering every contest for which I was eligible (resulting in unused Yanni tickets!). For total disclosure, I won those when I was a teenager with lots of time on my hands, so calling the local radio station fanatically wasn't a great expense and winning was a great reward. These days, I have less time on my hands, so I enter contests with more discretion and when they are relatively easy to enter, like with Wannawin.
2) Prioritize contests with attractive prizes. I enter every contest I can where I can win a Vespa (this is a U.S. contest - I make the most of dual citizenship!). I also love to travel, so I'm regularly on the lookout for great travel contests.
3) If there's a contest you really want to win, enter as often as you can. For example, I'm entering theCanadian Bacardi Break-Free from the Everyday contest, well, everyday (or as often as I remember) !

Here are a few links to some of my favorite contest listings and blogs:
- ContestCanada.net provides a great blog roll of current contests along with eligibility requirements (I'm often ineligible since Quebec has strict contest regulations).
- ContestGuide.com includes links to US and Canadian contests
- Sandra's Contest Blog is updated daily with links to some fantastic US contests.

Finally, a shout out to the Budgets are Sexy blogger for motivating me to write this post with his Amazon gift card contest, which you can enter to win with a comment on that post. Please also comment here with your ideas on contests and winnings!