My Secrets on How to Enter Contests…and Win!


My Secrets on How to Enter Contests...and Win!

You probably have a friend who always wins contests, right? She’s the “lucky one”. Why can’t you be the one to win?! You can! I am the “lucky one” and I’m ready to give you the secrets about how to enter contests and win!

Back when I was a girl (long before the internet, of course) my dad would occasionally receive a newsprint mailer that had national contests. I was intrigued by the thought of possibly winning a vacation, cash, even a car. I recall a few times, filling out postcards with the contest addresses as per the instructions and sending them off in the mail, fingers crossed. I never won anything, of course.

When I was in high school my dad won a contest in the newspaper to name a casino in Las Vegas. He was one of many who chose the name (“Excalibur”) and was awarded a weekend stay at the new hotel and my mom and he got all their meals for free. That was fun!

I won this two-day Disney vacation on the radio!

I won this two-day Disney vacation on the radio!

I’ve been pretty lucky through the years, including an appearance on Wheel of Fortune (won $5300 cash!) In the last few years, I’ve really devoted more time to contest entry and it’s paid off. Locally I’ve won San Diego Safari Park tickets, Disneyland Park Hopper tickets and an overnight weekend at the Disneyland Resort complete with 2-day park tickets for all four of us.

Online I have won cash prizes (nearly $3000 in American Express & Visa gift cards in one year), year-supply prizes (like King’s Hawaiian Bread and Campbell’s Soup), a set of my favorite dishes from Lenox, 3 trips (a weekend in NYC from Armitron Watches, 9-day trip to Europe from Skype and a vacation to Greece from the Greek Tourism Board), as well as over a hundred other things.

Winner, winner! A selection of kids clothes from Tea Collection.

Winner, winner! A selection of kids clothes from Tea Collection.

My motto: Someone has to win, why not me? 

You know, you can’t win if you don’t play. I am by no means a professional at this and there are many websites that will go into more detail but this is how I do it:

  • At least once a week, I do an internet search for contests that sound interesting to me and load the links into an Excel spreadsheet. There are websites that list tons of contests in a directory like Sweepstakes Advantage and Sweeties Sweeps. These are the two I use most. I like to look for specific contests too, like travel to Walt Disney World, and I find Disney-themed contest on Mousesavers.
  • I don’t enter contests with prizes I don’t want or need.
  • I do “like” certain companies on Facebook that run frequent promotions and then check their sites to see when they start new contests.
  • I also follow blogs that I enjoy reading and enter their contests as well. I won a gift certificate last year to Party Box Design on a blog and was able to get the baby’s birthday invitations designed for free. Some blogs have more complicated entry processes like tweeting, following their Pinterest boards, liking them on Facebook and others only require a simple comment.
  • I like Pinterest contests and essays best because they take a certain creativity. The Ellen Show frequently has essay contests with fantastic prizes.
Enjoying our trip to New York, courtesy of Armitron Watches.

Enjoying our trip to New York, courtesy of Armitron Watches.

Reading the fine print:

  • Read those Official Rules. Really. At least the parts that tell you how many times you can enter, how long the contest lasts, how the winners will be contacted and what it is exactly that you’re entering to win.
  • Pay attention to how many times you can enter. I steer away from contests that tell me I can enter “up to 100 times a day”. ‘Ain’t nobody got time for that! I prefer contests that only allow one entry per person/email address. This really evens the playing field. But if you’re in it to win it, make sure if it’s a daily entry contest that you really do enter every single day to get the best odds.
  • Look at the starting and ending dates of the contest. Try and get in on the beginning of the contest if you are able to enter once a day to give you the best odds. I’ve entered every single day for the HGTV Dream Home contest; technically twice, because they let you enter at both and They also offer a flooring contest from Lumber Liquidators & another for a GMC vehicle. I entered them all, every day of the contest so my odds are as great as they can possibly be! Of course, I’m in the mix with millions of others, but remember, someone has to win! Why not me? (or you!)
  • Some contests will ask for a code or something from a proof of purchase but there are often alternate ways of obtaining the entry (some as easy as just clicking a link that will supply you with a code without a purchase).
  • Watch those clickable boxes at the end of the entry form! If you don’t want to receive a bunch of unwanted spam or junk mail or accidentally sign up for something you don’t want (like a magazine subscription). Make sure you know what you’ve clicked (sometimes the boxes are already clicked and you need to unclick them each time).



  • Find your favorite stores and internet shops on Facebook and Pinterest and see if they are running any online contests. Click the Facebook “pages feed” to show the recent posts of those you follow. Many of these will host simple comment-and-win daily contests. I won a $500 necklace from Jared The Galleria of Jewelry this way!
  • Magazines often have contests or sweepstakes so a quick online search of your favorites should let you know what is available to enter.
  • Your local radio station probably has call-in contests (that’s how I won a $50 Macy’s card) but they often have online sweepstakes as well (that’s how I won the Disney tickets and trip!).
  • Blogs are great place to enter and depending on the number of readers/entrants, the odds can be pretty good!

Last of all, good luck! Be consistent with your entering, have fun and have hope. Don’t get discouraged if you don’t win anything. But at least you are casting your net and I have my fingers crossed that you’ll win a big one someday! Here’s to hoping we win ourselves a Disney trip and we can use the savings bank for souvenirs!



1 reply

Trackbacks & Pingbacks

  1. […] making time for blogging, I’ve cut back a bit on my contest entries but I did write a post on how the contest process works for me. Let me know what you […]

Comments are closed.