Become a Career Contest Winner and Save Money by Winning

28 October 2014


For some, entering contests and sweepstakes is more than just an occasional lark – it's their career.

I first became aware of these prodigious winners as a kid. The son of a friend of my father's, Jason Sheps, made entering contests his job and, as a result, he won a lot. In fact, he's still doing it to this day as an adult. When last I saw him, he had won seats in a suite at the Air Canada Centre for the Toronto Maple Leafs, had his mom's entire kitchen redone for free and took a boat trip in Vancouver with the Canadian Coastguard. His mother estimates that he's won thousands of dollars in services, vacations, food and merchandise since he started doing this in elementary school.

I know, just reading that makes it all seem way to good to be true, but it can be done and Carolyn Wilman has made a career out of teaching people how to do it.

She calls herself The Contest Queen and she makes a living auditing, creating and drafting rules for contests and sweepstakes. With a background in marketing and event coordination, she has over 25 years experience, both as a contest competitor and as a contest consultant. Like Jason, she started entering contests as a kid. She'd be one of those teens, hanging on the rotary dialer, hoping to be the seventeenth caller for concert tickets.

She has won contests big and small since she was 15 and has saved a considerable amount of money doing so. Breakfast Television, Canada AM and The Mom Show all wanted to know her sweepstakes secrets and luckily, I can share a few here that she told me when I interviewed her in 2010 and are featured in her book, You Can't Win If You Don't Enter.

Know How to Find Them

There are many contests to be entered – even more if you count those available through social media – you just need to know where to look and it's not always so obvious. That's why you should get to know contest aggregators like All Canada Contests, which list all legitimate contests available to Canadians on one website. There are many of these, along with newsletters, blogs, sponsors, and forums that all point in the direction of active contests. We have a weekly roundup of contests on Bargainmoose, so take a look for that each Wednesday.

Honestly, the amount of contests that are out there can be a bit overwhelming, which is why Wilman recommends joining only one or two of these places, so you can avoid potential duplicates and don't get confused.

Read the Rules Carefully

This is Wilman's #1 tip since so many people don't actually do it and screw up their chances of winning right off the bat.

“If you disqualify yourself and your name is drawn, you won't win -- simple as that. If you're not paying attention, you're just wasting your time,” she says.

The biggest rules that people overlook are the start date and the end date of the contest, so they're either too late to enter or they're unable to maximize their opportunities to enter because they don't start on the first day. Also, not all contests are open to residents of Canada and even if they are, Quebec is usually shut out due to strict provincial government regulations for sweepstakes that are meant to protect citizens from scams. Some contests are only open to kids and some limit the number of times you can enter, either per day or for the duration of the contest, so read the rules and fine print carefully.

Enter as Many Contests and Sweepstakes as Many Times as You Can

The greatest key to making contests a career and winning a lot is to enter as many as you can as often as you can.

“It's a numbers game,” says Wilman. “"I win 1% of what I enter," she says. "People think I'm so lucky, I win everything, but 99% of those prizes go to other people."

Her average output is about 100 to 300 entries a day, which equates to five to 15 prizes a month. It may seem like an epic waste of time at first, but Wilman says it does pay off.

“My husband used to tell me this was a waste of time and it was just a silly hobby, but then I won him the right to be a judge at the Miss Hawaiian Tropic Bikini Contest and he shut up pretty fast. Suddenly, it became 'When are you going to enter that contest?'”

Also, there is technology out there that makes it so much easier, which leads to her next tip.

Use Technology to Your Advantage

There's nothing in the rules that says you can't use technology to make entering contests easier for you and that's exactly what Wilman recommends. She uses a tool called Roboform to help her fill out multiple entry forms at the same time and organize them from one central hub. Through her $30 investment, she has won over $200,000 in prizes, so it's pretty worth it if you're going to be serious about this.

Don't Work Alone

The good news is, you don't have to enter contests in isolation. You can build a support system to help you out and give you tips along the way, especially because contests are getting harder and harder these days.

“More and more they're looking for UPC codes, they want skill testing questions and you can get help from other people,” confirms Wilman.

To stem the tide and fight back against the increased complexity, Wilman recommends starting a contest club in your neighbourhood where friends can get together and “talk shop,” as she calls it. It's a great way to pool your resources and collect the required number of boxtops or UPC codes faster. Besides, while Wilman admits that the contest internet forums can get really clique-y and snippy, she says you won't have the same problems as much in real life.

“You find the right group and everyone is happy for you, you don't get the eye-rolls and the jealousy.”

Do you think entering contests to save money is worth it? Let us know in the comments below.

Photo credit: Ben Rea


  • Shar
    I was not able to click to join their mailing list, anyone else having trouble with all Canada?
  • Lucie
    I love to enter contests when the odds are better to win. Forget about lotteries, I've won great prizes at store anniversary sales, promotions, and smaller prizes on Internet draws. My last big win was at Leon's last Xmas. I chose what I wanted to win which was a washer, dryer and took a pick of the prize with Santa. The odds of winner at a local store is much higher than a provincial or national level. Try it! You might just come home with a treasure and a great story.
  • Linda P.
    I have been doing it for 10 years and love it. Not all years were profitable, but always managed to get something every. I have won Lazy Boy recliner sofa, a trip to Florida and dozens fo week ends to hotels around the province, and I only work on it for about 3 hours a day, just do it for fun.
  • Lillian B.
    I have won lots and lots…. $20,000 SCJohnson-$5000 HGTV-$4000 travel credit-Apple iPad-ipad touch-ipad nano-11 in Apple notebook-3 cameras- $1000's in gift cards-$1500 worth of snowboard gear and clothing-over $2000 in toys and games-trips including New York and dozens of free hotel nights-in the past 3 months I have won $2000 in patio furniture and BBQ-$700 in heated patio stone-$140 worth of makeup-4 GC'S for Shoppers from diff giveaways -$1000 prepaid visa ...I get to pick up Monday plus too much to list-I spend 2-3 hours in total per day and my family and grandchildren love it. My neighbour mentioned today that I must be winning a lot as UPS are here 2 or 3 times a week-one different prize was Majesta paper products for a year but there was more than a years worth, and the product was delivered (not coupons) but cases of product-UPS made 2 trips and there were 11 huge boxes -that was 18 months ago and I have enough toilet tissue for another year as I have won more since then. Won $500 gc for Boston Pizza and Pizza for a year from Pizza Delight. I win at least once a week and last week had 3 wins-Love It!!!!

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