Why Am I Not Winning?

12 Expert Tips to Winning Prizes More Often


Every single day I get messages asking the same thing..."Why am I not winning!?"


It's an amazing feeling to get a free prize in the mail that just makes your day!

Many people see others winning amazing prizes and think it must be super easy to win! Well it's not super easy for someone just starting out in the fun and rewarding hobby. But it does get easier in time when you get a few tips and tricks under your belt.

In the private My Canadian Mailbox FB group lucky Canadians share their prizes won every day all day and there is a reason for that. The reason? Persistence and learning.

As with anything you do in life learning the ropes and the how to's of a hobby is very important. Reading is your best chance at winning prizes more often.

Expert Tips to Start Winning.


1. Use a separate email for all contest and giveaway competitions.

Having an email dedicated to only competitions will help you stay on track with daily entries, keep scams at bay and make winner emails easier to spot.

2. Start Entering Local Contests

Local contests are everywhere. Your local radio station probably has 2 or 3 a week. Local malls and stores often have amazing giveaways and competitions to win prizes right in your own town or city. These contests are generally easier to win, and once you win once it gives you the motivation to really amp up your contesting skills.

3. Contesting Time

Set aside time single day for your contest entering and competition hobby. Late night relaxing bath? Grab your tablet  or cell and enter contests while you relax. Have a few minutes with your morning coffee? Put 20 minutes towards entering and winning some prizes.

As with any hobby the time invested will help you win more often and yield more prizes in the long run.

4.  Avoid Spammy Freebie and Coupon Pages

There are so many people that are upset they aren't winning prizes and never do, but where they are entering these contests is a dead end. There are certain contesting websites for Canadians that just won't lead you to winning prizes.

5. Accidental Cheating is still cheating.

Avoid cheating at all costs, even accidental cheating can will disqualify you from winning a prize right out of the gate. If a contest states you can only enter once, don't enter once from 10 emails. Its cheating, its fraud and you won't win.

6. Stop Skimming

Don't just glance at the T&C's and think you understand. You could be signing yourself up for a ton of spam to even agreeing to having your information sold. Reading the full rules and regulations can actually help you win more!!

READ ALSO: 6 Crucial Tips to Winning Instant Prizes

Example: Oreo instant win contest's rules share information with you about prizes and on what days prize. But if you failed to read the rules you could be entering only on days that there is one prize to win. You lower your odds of scoring a prize by not reading the rules.




7. Stop Entering Everything

Many full time contesters will tell you the more you enter the less you will win and it's so true. If you simply just enter everything you see, you are more than likely missing out on prizes.

Be picky and specific about the contests and giveaways you enter. Having a bucket list of prizes you would ultimately like to win can actually help you win more often.

Think of it this way....If you really want to win one of the prizes a contest or giveaway is offering, you are more likely to come back daily for you extra entries, check back on the giveaway at its close date, follow up and see a winners list.

If you are a 24 year old female living in a big city and you win a tractor from a random contest you entered...? Think you will be oh so excited? You probably wouldn't even know you won because you lost interest the second you left the contest page.

  • Write yourself a prize bucket list
  • Bookmark contests and giveaways to check back and do all the required daily contest entries.
  • Focus on your bucket list of prizes you want to win. Search online for those specific giveaways and contests. ie.. If you want to win a guitar, search "guitar giveaways".
  • Always perform all the actions a contest asks for. Your chances of winning will increase.
  • Be realistic with your bucket list
8. Take full advantage of bonus entries

When you enter a contest and there is an option for bonus entries take advantage of those options. Having a great network of friends on social media that love contests too can really help you and them. When you share your referral link to Twitter or Instagram make sure your profile is set to public.

Reading the rules regarding referral entries is so important. Did you know MANY contests have right in their terms that you MUST KNOW personally the people you refer and that they can ask for proof of that when you claim your prize? Not all contests add the term in, but make sure to check the full rules when referring.

9. Search for your own contests 

Stop relying on contest and freebie pages to lead you to contests and giveaways. Learn to find contests that have prizes from your bucket list in #7.


Searching to win a trip? Search it different ways:
  • Win a trip
  • Win a family trip
  • Win a trip for two
  • Trips to be won
  • Trip giveaway
  • Contest trip to Canada (Insert your dream place)
Tip #1 

Make sure your Google search engine bar is set up before you actually search. First type in a prize you are looking to win - Win a Trip hit the search button. Now don't look at the results yet you will be wasting your time. 

Under your search bar is your search engine settings. Pick your country, and in the next tab pic the time limit. Make it within last 24 hours or past week. Then hit search again and now you have valid and current trip contests open to your country. 

Tip #2  

Adding a minus sign in front of a word in your search will eliminate that thing or place from your search which will narrow your search down even more. 


10.  Your Profile Could Stop You From Winning

This is a big one. Your social profile on Facebook, Instagram, Twitter, Pinterest and so on, should all be in your LEGAL NAME. Many high value contests ask for your photo identification and if the name doesn't match your online social profile name you entered with you forfeit your prize. 

If you are wanting to really win more prizes and begin contesting as a hobby make your profiles contest worthy.


11. Stop Writing Mindless Comments

Too often on contest and competition posts you see the mindless comments like these:

  • "Pick me" 
  • "I want it"
  • "Me Please"
  • "Send it to me"
  • "I wan't it"
  • "I need it"
  • "Win"
  • "Liked & Shared"
Comments like those will get you overlooked every time. Comments that are mindless show the contest holder you could care less about their contest or product, so why would they ever pick you?

12.  Positive Thoughts

Thinking positive thoughts  can bring you some amazing luck and not just in your contesting hobby. Positive affirmations can do wonders and spur you to continue entering and start winning more often.

Learn to expect good fortune and be optimistic.