So one thing I got back into (a bit more heavily) than in recent years, has been sweeping. For those unaware, sweeping is simply a fancy word (not that fancy to be honest) for entering contests. Determining which ones to enter, can be tough for someone trying to get into it, and getting the "Sorry, try again" message, certainly after you enter Instant's (will get down to that in a bit) can be a detriment that could get you to stop entering contests (did for me a few years ago).
Now there are different types of contest you can enter. There are dailies (one's you enter everyday), there are one time entries (these are the one's where you enter once and that is it), and then there are instant's (these are the one's you usually enter everyday, or in some occasions only once, but unlike the other two categories, you find out if you've won right then and there after you are done entering). As far as where you find these contests, I recommend three forums. They are in order, and are as follows: Slickdeals CAG and Online-Sweepstakes
Now there is a whole other world of entering contests, and with that, I'm referring to twitter. I have been fortunate enough to win some nice prizes from twitter this year, and in all honesty, the past two years. As far as whom to follow, I would recommend first creating two lists. Two that I follow are: http://twitter.com/#!/PrinterStop/contests and http://twitter.com/#!/Gadgets4nowt/xbox-360-comp-entries Secondly, if you see users that are constantly entering contests on twitter, it would be smart to follow them, or bookmark for future reference (as you are only allowed to follow 2,000 people before you can't follow anyone else (assuming you don't have that much that's following you).
Lastly, my advice, is to just enter to enter. Don't enter expecting you will win (as you will burn out, and gradually stop entering altogether). The phrase "I'm not lucky enough," or "I'll never win" only holds true, if you never enter. You have to enter to win. Remember that.
I will list things I've won as a reference to show that it is possible to win:
Necklace (waiting for the right moment and person to give this to, to be honest)
Signed & Framed Andy Roddick Tennis Racket (Substituted for a Professional Display Samsung LFD Display Monitor, worth $2600+)
USA Network Summer Beach Swag Bag
Countless movie tickets
Battlefield 3 Vault
Modern Warfare 3
Movie Promotional Items
Tickets (8 to the circus, 4 for a concert at Honda Center, 4 for Aquarium of the Pacific)
and lots more.
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