
This is a guest post from my super best friend Sunshine over at Transforming the Now. She has been contesting for over a decade and has the swag to prove it. Her success can be your success! She tells us that we don’t have to be prettier (handsomer?), smarter, or luckier than anyone else. We just have to be persistent. Seriously. That’s all it is. Read on to learn more:
Have you ever read about those people who win stuff all the time? Those ‘contest junkies’ or ‘sweepstakes crazies’? Ever wondered who wins all that stuff? Or thought that it must be a hoax?
Let me tell you how that looks from my side of things. We’re leaving for Australia in seven weeks. Air, hotel, tours, and transfers paid for, e-tickets dangling cheerfully on the fridge. The only costs that we paid for were air taxes (approx. $150 each) and a few additional nights of hotel to extend our stay.
This follows up our last trip three years ago, where we spent 3 weeks wandering through Florence and Rome, part of our trip spent in a suite in a castle in the Tuscan foothills.
And the trip before that, which was our honeymoon in New Zealand, complete with a visit to Bilbo’s house and to pay homage to the Party Tree. (Those of you who are LOTR fans understand immediately.Those who don’t will need to request clarification from the Gods of Google).
All of these things have been contest wins. All paid for by the contest sponsor (although two of the three we paid air taxes of between $150 and $250 per person), and all through the wonders of winning. Hoax? No. Crazily insane, inimitatable, horseshoes-somewhere-
Contesting: How it all began

Let me tell you a story. Back in my early 20s, I entered a contest online on a local magazine. Promptly forgot about it, and continued on my regularly scheduled life. A few weeks later, a package notice arrived in my mailbox.
Hmmm – I hadn’t ordered anything, my birthday was not for months, and Christmas was long gone. When I opened it, it was a prize pack from the contest I had entered. Nothing spectacular – a book about a girl boxer movie (not the Hilary Swank one, WAY prior to that), a CD, a $5 gift card, and a couple of pens. I know – not worth proclaiming from the rooftops.
I gave the CD and book away, used the gift card, and put the pens in my purse. But a light went off in my head. I hadn’t done anything for this. I didn’t have to work for it, pay for it, trade for it. I had just filled in a form online, and then free stuff magically appeared at my door. This was just a few odds and ends…but what else was out there??
Contesting: What are the numbers?
And so, my friends, it began. What you do all the time matters MUCH more than what you do once in awhile. And what I do all the time, you see, is enter contests. Somewhere around 70 a day. Every day. Weekends and holidays included. You know what this girl was doing Christmas Day, before she was allowed to have her turkey? That’s right.

Let’s do the math on that, shall we? 70/day works out to approximately 2100/month, and 24,000/year. That’s a LOT of contests. And it pays off. When you enter that much, you will win. A lot.
Update:
I had some requests for what this would look like on a per hour basis. As it works out, Sunshine makes $55/hour based on contesting for one hour a day, thirty days a month, every month of the year. This is based on her January to August winnings of this year. What about other years, you ask? Surely that $10,000 win in January is an anomaly. In my time of knowing Sunshine, she has won a big trip/prize three out of the last six years.
Check out the prize breakdown by month here. The link is to a Google documents attachment.
Here are some tips:
*pick a time of day and always enter at the same time. It creates a habit and then it’s easier to continue.
*use a form filler (such as Roboform) to speed up the process
*use dedicated contest sites like contestgirl.com or contestcanada.net. They have contests divided into all different categories and helpful little functions that will make entering giveaways a breeze.
*the contests with the best odds are blog contests and contests that are local to you (newspapers, TV stations, radio stations, etc)
*if you don’t know what the company does, makes, or sells, you probably shouldn’t enter. That way, scammers live. If the website looks poorly put together but the prize is really good, it’s probably a scam. If anyone tries to get your credit card number, it’s a scam. If the prize is over $200 and there’s no release form, and you haven’t heard of the company before, it might be iffy.
*do something else at the same time…it’s really very, very boring. Talk on the phone, listen to the radio, whatever works for you.
*pay attention to the rules. If it says you can enter once a day, enter once a day. Or once a week. Or whatever. If you need to be a certain age or doing a certain job to be eligible, make sure you meet the criteria. There’s no bigger bummer than getting a win only to be disqualified.
*don’t enter for things you don’t actually want. It’s bad contest karma. (Exception: You’ll occasionally enter for something you really want, like a trip to the Superbowl, and win the third runner-up prize, which is a randomly NFL-signed football that you have no interest in. That’s okay. That’s what Christmas toy drives are for)
*set up a separate email address, check it religiously, and make sure to keep your filters low so that you don’t miss anything.
End of Update
Contesting: A Lifestyle Upgrade
I have won a flat screen TV, when it was cutting edge technology. A new computer to replace my old one, which, naturally, I used to enter more contests. My honeymoon, where we ended up going on a trip to New Zealand when we had figured on going camping with the meagre funds we had. $7500 in travel credit to go anywhere in the world, which culminated in three glorious weeks in Tuscany, with a beautiful hotel in the centre of Florence and zooming around in an Alfa Romeo.
Crazy experiences like a celebrity party to introduce a new brand of Peroni, held on the rooftop garden of a luxury hotel, front row concert tickets, enough movies that I rarely pay for them anymore, and lots of truly random stuff. Singing, battery-powered One Direction toothbrushes arrived recently in a prize pack from Arm&Hammer. Weird? Deeply. But there are some very (squealingly) delighted teenage daughters of an acquaintance who cherish them.
The mail doesn’t mean bills to me. It means interesting packages and an endless series of possibilities. I probably win once every week or two, anything from movie passes to a fabulous trip somewhere or tickets to a concert I’ve been dying to go to but can’t afford.
Entering contests is a lifestyle choice. It’s not a job, precisely, as there’s no guaranteed payoff, but it makes a bunch of wonderful extras financially viable. Yes, it’s 45 minutes less sleep in the morning. Yes, it’s INCREDIBLY tedious. And yes, I get a TON of junk mail. But since I get to go through it on glamourous vacations that I could never otherwise afford, I’m totally okay with that.
So for all of you nay-sayers out there, go ahead and nay-say. For those of you who want to take up the contesting chalice, see my contest post here for the how-to:
Contesting:The Ultimate Lifestyle Upgrade @ Transforming the Now
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