How Do I Win Big?

question markCarolyn,

I don’t know if my question is blog-worth, but here it goes: I’ve noticed the same few people posting up daily/weekly/monthly with all kinds of extraordinary wins ($1000 here, a trip there, etc.)  It may be a broad question, but how do the same people see to keep turning in these enormous wins??  I’d like to learn their secrets and be a better sweeper.  I saw a few people post they broke into six figures last year with their wins, and I’ve never broken $3500.00 for the year.  It certainly makes me think I have a lot to learn.

Thanks as always, Carolyn.

Your question is so blog worthy! I sometimes wonder the same thing! (In Canada it is harder to win prizes as they are further and fewer between.)

There are several potential reasons why you may not be winning big.

  • You are not organized. Being organized saves time, therefore you can maximize the number of contests you can enter in a shorter period of time.
  • You are wasting your time. What are you entering? Enter single entry sweepstakes first, then those with a higher dollar value prize, then instants, then dailies. Do not waste your time trolling Facebook for timeline contests or Twitter for retweet contests. Those you do from your mobile while waiting in line.
  • You are not entering best odds sweepstakes. This ties back to point #2. Entering low value, low odds sweepstakes are only netting you a few thousand dollars in wins over the course of a year. You can find best odds sweepstakes on Sweeties Sweeps, Sweepstakes Advantage or Sweepstakes Fanatics.
  • You are not entering enough. If you enter for 30 minutes per day and I enter for 4 hours, my odds of winning are going to be far greater than yours. I recommend entering 1-2 hours per day. That’s enough to win well, but not so much you cut into work, family time, and any other obligations. Winning should always remain a hobby and not reduce the quality of your life.
  • You don’t know how much you won. I used to think I didn’t win very much. So one year I decided to track every win. I mean every win. From a free coffee or bag of chips through to electronics and trips. I discovered I won far more than I originally thought. You can track your wins using my winning spreadsheet.

Be aware, not everyone posts their wins. There a lot more winners out there than you realize. Some win more than you, and some win less. You just don’t see it. I stopped comparing myself to others a long time ago. I win, what I win, when I win it.

Sandra Grauschopf also wrote an extensive article on your exact problem. Not Winning Sweepstakes? How to Deal with Sweepstakes Frustration

If you have a sweepstakes, contest or giveaway question, please email me.

2015-08-04T13:53:27+00:00January 24th, 2015|Featured, Your Questions Answered, YQA|10 Comments

About the Author:

Carolyn Wilman (aka @ContestQueen) is a Digital Marketing Strategist and Sweepstakes Specialist. Carolyn teaches others how to Find, Organize, Enter and Win giveaways along with working with companies to create, and viral market, winning promotions maximizing ROI and loyal customers.


  1. David Balkin January 24, 2015 at 9:42 am - Reply


  2. Belinda McNabb January 24, 2015 at 11:56 am - Reply

    You always give us such great tips and insight! Thank you. Working/family and trying to balance it all can be tough. Trying to keep contesting a hobby and something I enjoy doing is key for me. Balancing contest entering along with family/work being the most important. I keep a spreadsheet of my wins to and it is pretty cool to watch the toatal wins for the year. It is pretty cool to watch the number go up!

  3. Linda Clineman January 25, 2015 at 6:40 am - Reply

    Good posting Carolyn – thank you for the refreshers.

  4. Lisa Coomer Queen January 25, 2015 at 10:03 am - Reply

    Thanks once again for the great tips!

  5. MaryJo Tsitouris January 25, 2015 at 11:29 am - Reply

    These are great tips. Sometimes I feel like I’m all over the place with absolutely no organization to my entries. I have also often wondered where to find lower-entry sweeps, but never knew where to look. Thanks for your tips!

  6. Christina Zawadiwsky January 28, 2015 at 4:18 pm - Reply

    There’s organization and thoughtful entering, but I would guess that luck enters into the equation, too. Read Carolyn’s book to learn how to bolster your luck!

  7. Tammy OHagan February 14, 2015 at 12:55 pm - Reply

    Love the article! I have a question.. How would you suggest organizing your list of snail mail sweeps and text 2 wins, etc I have them written in a notebook, but find that I occasionally overlook one or two. Is there a “program”/ database we could use?

  8. Bill Monson June 7, 2015 at 4:18 pm - Reply

    Hi Carolyn Wilman,

    Great website, So much to learn here 🙂
    Which Contests/Sweepstakes have you had the best chance of Winning Big prizes on: Websites, Snail Mail, Text or Store Purchases?

  9. Willie H. November 3, 2016 at 2:25 pm - Reply has a great newsletter that focuses on sweeps with great odds. How do you leave them out?

    • Carolyn
      Carolyn November 3, 2016 at 7:37 pm - Reply

      I am good friends with Tom (the owner of IWINContests). He understands I like to be fair and share the spotlight amongst all those in the hobby. Trust me, I give Tom lots of kuddos on various platforms. He was even the editor of my latest book!!

Leave A Comment

This site uses Akismet to reduce spam. Learn how your comment data is processed.