I read an article about the “Contest Queen,” aka Carolyn Wilman, who has won over $250,000 in prizes from entering sweepstakes. She has been a regular winner since 2004, with prizes ranging from a bottle of pop to a trip for four to the 2010 Vancouver Winter Olympics – just one of 16 trips she has won.

I suggested to my husband that he enter online sweepstakes and surveys. After all, he sits around mostly doing nothing. Maybe we could win something.

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He was eager at first, but after a few weeks he gave up. “This is stupid,” he said. I guess he was not patient or persistent enough, or have the luck of these regular winners:

  • Eleanor has won trips to Arizona, Virginia, San Diego, Chile and Israel, several pairs of $500 shoes, diamond jewelry, a LaCrueset casserole dish, blow drier, high end skin products and makeup, food products and cash – to name a few.
  • Lindsey just won a giant screen LED TV and has also received concert tickets, spa treatments, a visit to a movie set, and an iPod.
  • Annalisa won a Toyota Prius, 3 trips to the Caribbean and one to space camp, jewelry, spa treatments, gift cards and cash.

Of course, not all wins are for big prizes. Your odds are actually better for the smaller prizes – handbags, towels, socks, baby items.

What are the odds?

Many newcomers to the sweepstakes wonder whether they’re entering enough contests. How many do you really have to enter to win?

According to Linda at contest girl, you will win if you keep trying. She wins multiple times each month.

The time and energy investment can be staggering, though. The most dedicated “sweepers” devote a portion (several hours) of each day and can enter up to 400 contests a week. Some people do it for a living!

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If you enter only a few contests it can take a phenomenally long time to win, by which point many people, like my husband, have given up.

Tips to increase your chances

Here are some tips if you are interested in trying this.

  • Get a form-filling program to speed up the entry form completion.
  • Enter as many contests as possible. Enter “daily entry” sweepstakes daily.
  • Check social media sites or search Google for “contests.”
  • Be organized and keep track of your entries.
  • Enter essay and photo contests for greater odds of winning.
  • Be selective. Don’t waste your time entering for a prize you don’t really want or couldn’t easily sell or give away as a gift.
  • Create a new email address solely for your sweepstakes entries.
  • Always read and follow the rules carefully.
  • Never pay a fee to enter, or give out your credit card number.
  • Thank the sponsors when you do win a prize.

Will my privacy be protected?

Unfortunately, the answer is almost certainly, “NO.” Read the fine print. Companies should disclose what they will do with your personal information, but keep in mind that they will probably sell it anyway, even if they claim to respect your privacy.

Related: My loyalty never got me a free 42″ TV

It’s up to you whether you want to trade the opportunity of winning a prize for a slew of emails in your in-box.

Have you ever entered online sweepstakes and won?

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