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.

Related: Dreaming of a lottery win

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!

Related: Could a lottery boost our savings rate?

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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6 Comments

  1. Tom on June 30, 2015 at 11:24 pm

    Back I think like 4 years ago or something ING Direct (now Tangerine) had a Facebook contest called like Flip To Win or something. Anyway, it was like a 4×4 grid of cards and they had either 5 or 10 xBox’s up for grabs (you click a card, if it had an xBox on it in stead of the ING logo, you won an xBox). Anyway, you could flip 3 cards a day or something and it was open to anyone who had a Facebook account and liked their page. The contest ran for a month.

    Long story short, I flipped every single day and my partner thought I was crazy, saying I’d never win. Then I did. So of course, it motivated him to try it out and a few days later, he won as well.

    Of course, it was limit 1 per household, so we did not end up receiving both of the game systems. But we thought it was pretty crazy that we both ended up winning. Gave the system away as a Xmas gift. Haven’t entered online contests since. Always feel like it’s a waste of time – too many scams out there anyway and my email gets enough junk mail!

  2. Tracey H on July 1, 2015 at 5:55 am

    Don’t bother. I’ve been entering contests since 1987 (mail-ins, in-store and radio in the early days, moving to the internet in the mid-90s). The days of easy winning (when I racked up well over $100,000 worth of prizes–I lost count after that total) are long over. I still spend hours every day entering and seldom win anymore (it’s become a habit that’s hard to give up, but I really should give it up). There are just too many people entering now.

  3. Carolyn Wilman on July 1, 2015 at 7:48 am

    Great post! The only comment I have is: I wish you and your hubby didn’t give up so soon. It’s one of the biggest mistakes people make when they are a newbie.

    Here are a few posts I wrote on the subject:
    http://www.contestqueen.com/2015/how-do-i-win-big/
    http://www.contestqueen.com/2015/the-best-sweepstakes-advice/
    http://www.contestqueen.com/2013/use-the-sales-funnel-to-win-prizes/

    Maybe you and your hubby will start entering again!!

  4. Kurt on July 1, 2015 at 8:27 am

    I’d rather just go to work every day and just buy the stuff I actually need and want. This is as bad as that stupid coupon show. Like we really need more “stuff”. When you’re validated by how much you have, your life is pretty empty.

  5. Cool Koshur on July 1, 2015 at 12:04 pm

    Online sweepstakes are a scam and not worth my privacy. First thing you notice is unsolicited emails in your Inbox, phone calls any time of day and night, lot of junk in your regular email.

  6. Carolyn Wilman on July 2, 2015 at 6:04 am

    Yes Tracey, it is harder to win big now, but it doesn’t mean you can’t. Read my blog post on the topic: http://www.contestqueen.com/2015/how-do-i-win-big/

    Kurt, the thing about contests is you can win things money can’t buy. Like the time I met Sting or my ex was a judge in the Miss Hawaiian Tropics Bikini Contest. Plus winning things I need and could buy, like a new hand mixer, saves on my budget. So are things like movie, concert and theater tickets.

    As for an email inbox full of junk, 1) I have a separate email address just for entering and 2) I teach people how to keep the junk to a minimum: http://eepurl.com/brxyzH

    I wonder what I’ll win today?

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