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Why Don’t I Ever Win Contests and Giveaway Prizes?

Feeling like you never win contest and giveaway prizes? Ready to give up, when all you see is everyone else winning prizes? It could be some very simple things that are holding you back. This post your one stop spot to get you started actually winning prizes!

The proof is in the pudding with all the prizes I win that the tips here work! You can also see how many real people just like you are winning prizes by checking out my private group Contesting with Confidence in Canada.

Each section in this post is something you need to look at before entering contests. 

Tip : Don’t ever utter the words “I never win” Thinking positive is the very first and most important step to winning prizes. Think like a winner and you will be a winner!

There are some very basic things stopping you from winning prizes : Entering the wrong ones, Disqualifying yourself, entering contests with very low odds of winning, being tricked into fake contests and entering at the wrong time of day.

There are some things I avoid altogether when it comes to entering contests. Things like entering contests posted on Freebie pages and websites.

Simple things like not seeing that you won a prize, could cost you a win you didn’t even know you won! That happens way too often to people.

With any new hobby we make mistakes. Making simple mistakes when contesting happens a lot. There are some very common mistakes you could be making that are holding you back from winning prizes.

#1 Entering the wrong contests is the number one mistake people make. 

Entering contests not open to your city is a complete waste of time. Entering contests that have ended and the form is still up, is a waste of time. Making sure to enter the right contests that are currently running and you are eligible for is the only way to start winning prizes.

#2 Not reading the rules and regulations in full before entering

As for Canadian contest law rules and regulations are a must for all contests. Reading them is so so so very important!! Not only reading them, but reading them twice. There is a wealth of information in the rules that can actually help you win a prize. Look for end dates, amount of prizes and how many times you can enter. If it’s a daily entry contest bookmark the contest and get those daily entries in.

#3 Not entering enough contests or doing your allowed amount of entries per contest

Entering a couple contests a week is not nearly enough to start a winning steak. People winning prizes regularly are entering tons and tons of contests to win about 1%-2% of them. It takes some effort to start the winning ball rolling. The more contests you enter, the better your odds are of winning prizes. Making sure to get the maximum entries in to each contest is key too.

#4 Missing Winner Notifications

Often people who think they never win prizes have won them! They just didn’t know and missed out on claiming them! Knowing how to deep search your emails for winner emails is important. Checking back on social media giveaways to see who is the winner is, can help you not miss out on a prize too.

Where Do I Find the Best Contests to Enter?

Entering just any contest you come across is not the best way to go about contesting. Doing targeted Google searches is a great way to find contests open to your country. Just typing in a random search into Google isn’t going to bring up the best contests at all. Tweaking your searches will do wonders. Local contests are your very best bet when you are first starting out entering contests.


When I first starting contesting a million years ago, I entered every contest I saw! What a mistake and such a big waste of time. Focusing on prizes you want to win, is the best way to see results. Having a contest bucket list can really keep you focused on finding the right contests.

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