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Meet 'The Contest Queen,' the woman who's won over $250,000 in prizes

·Nezihe Soyalan

On the sweepstakes printed in big red letters, it reads “Enter for your chance to win.” You think to yourself what are the odds of winning? Well, if you’re The Contest Queen, your odds are pretty high.
We all dream of winning that grand prize, and Carolyn Wilman has strategies that's helped win her over $250,000 in prizes.
Wilman, 48, a Canadian author of two books on the subject, always loved the idea of winning contests. Her first big win was at the age of 14 when she called into her local radio station and won tickets for a Burton Cummings concert. “I was too young to pick up the tickets myself so my mother had to go in and pick it up for me,” she says.
Years later, unemployed and curious about sweepstakes, Wilman read an article in Reader’s Digest about a couple who had earned their living entering sweepstakes. She figured she could do the same thing. Well, not quite. She doesn’t make a living “sweeping,” as it’s called, but she says it definitely enhances her lifestyle.
Wilman has won everything from a bottle of soda to a trip for four to the 2010 Winter Olympics in Vancouver. In total she has taken 16 trips of a lifetime – and none of it on her own dime. Some of her wins include a trip to London for a Harry Potter-themed costume dinner party dinner, a European Discovery 14-day Tour, a trip for two to Santorini, Greece, and a trip for two to Santa Fe, N.M.
Her winnings became so regular that in 2004 she started keeping spreadsheets to track the value of her prizes. Her best year to date is in 2009 when she won $68,491 in prizes.  (Sweepstake prize winnings are not taxed in Canada, but depending on specific rules for some promotions, she must pay travel-related fees.)
With estimated 55 million Americans entering sweepstakes each year, Wilman blogs to help others enjoy – and profit from – the hobby as well. “Some of the people have actually won more than I have,” says Wilman. “I’ve helped a woman win a house. I’ve helped someone win a Ferrari. I’ve even helped someone win a trip to outer space.”
Here are a few tips from Wilman on how to become the ultimate sweeper:
1. Use a separate email for sweepstakes. It separates your personal emails from your sweepstakes emails and it makes it easier to sort and find.
2. The best place to find sweepstakes. So-called aggregate websites, which Wilman lists on her site here, are the best source for finding legitimate promotions because the sweepstakes included there have been vetted. “The people that are posting on there have glanced at the rules, have checked out the site, they’ve seen the advertising,” Wilman says.  

3. Always read the rules. This is an important one, Wilman says. It pays to read the fine print so you can distinguish between a legitimate promotion and a scam (scams will look suspect and hardly include any rules). Also, different sweepstakes have different eligibility rules, so read the fine print to make sure you’re qualified to enter.
4. Start local and then broaden your scope. To save time and increase your odds of winning, Wilman has a strategy. She suggests starting with local sweepstakes, which have fewer entries and therefore betters your odds of winning. Then go statewide, and then onto the bigger, national promotions that get higher numbers of entries.
5. Don’t spend more than an hour or two entering a day. Despite the prospect of winning a new Mercedes–Benz C Class or a vacation to Sandals resort in the Bahamas, don’t let sweepstakes take over your life. Wilman stresses balance. She says: “You do not want this hobby taking away from family time, obligations, your job”.
Happy Sweeping!

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