Is entering Sweepstakes and Contests a debt payoff strategy?

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Spoiler Alert: Absolutely not. However, it’s a lot of fun and as my dad always said about the lotto, “you can’t win if you don’t play”. Out of all the advice he has given, that might be the only one that stuck.

One piece of Dad-advice that never stuck was, “always get a receipt at the gas station. That way, when you drive away and the cops pull you over for stealing gas, you have proof that you paid for it.” 

“Sweeping” is a term describing serious sweepstakes applicants who enter sweepstakes on a regular basis. You might be thinking, “why would someone spend their free time entering contests when the chances of winning are absolutely minuscule?”. Those “sweepers” have found that a few tips and tricks can increase your odds of winning, landing them some big prizes. A free vacation, a new car, a year of free groceries, etc. Wouldn’t that be nice? Well, you “can’t win if you don’t play”. 

But what if we could increase our odds of winning? Those “sweepers” have unlocked the code for us, so here are their tips & tricks:

  • Create an email just for sweepstakes entries. You’re going to be on a ton of new newsletters, so this will ensure your regular inbox isn’t overloaded with emails. 
  • Use a Sweepstakes Aggregate. An aggregate is a website that lists all the good sweepstakes in one spot. I really like . You can sort available sweepstakes by the prize offered, entry limits, and how soon the contest ends. But there are a ton of them out there. 
  • More effort = Better Odds (sometimes). Enter the sweepstakes that require something beyond just filling out your information. This is where you really start to increase your odds of winning. The effort of taking a photo for a contest or creating something keeps some people from entering. Take advantage of that! I recently entered a contest through Affirm where you needed to create a 30 second video with your findings of some “gotcha” language in a company’s terms and conditions. So first, I had to find some good “gotcha language” in terms & conditions. That was super boring…no one likes reading those. And that’s the point! Then I had to find a creative way to present my findings. It could have been with a dramatic reading, a puppet show, an interpretive dance, whatever we wanted. So I taught myself how to create and edit films with iMovie on my Mac and created a 30 second clip with this information. A bit of hard work, but ultimately the prize is $10,000, so I’m ok with that. Keep all your fingers and toes crossed that I win.
  • Stay organized! Keep a running list of what you enter and what you win. By looking at these different wins, you can see trends in your wins and losses. Then focus your entry efforts into the types of contests you win more often. Like Shakira’s hips, the data doesn’t lie. Also I’m a lady in the streets and a freak in the spreadsheets so you know I keep a spreadsheet on this.
    • You can download my Sweepstakes Spreadsheet with the download button below. Delete the data, add your own entires, wins/losses and track your progress.
    • I also have a tab with multiple pivot tables which breaks down my % of wins and losses by entry type and company/sponsor of the sweepstakes. When I see where my odds are better, I enter more contests with those companies or application styles.
    • This also makes it easier to list out your winnings when doing taxes (if applicable where you live).
  • Use form-filling software to complete entires quickly. has a free tool, or I use the auto-fill feature on my iPhone. I personally will never add my credit card information to any auto-fill software. But I’m also paranoid about that stuff…to a fault. I still shred a lot of my mail and have an RFID-blocking wallet so no-one scans my credit cards while walking around a grocery store. Crazy? Yea, probably. That might be that Dad-advice coming into play. Do what makes you comfortable. But the auto-fill feature does make the entry process faster. 
  • On a similar topic to payment information, avoid anything that requires paying for entry or paying to receive a prize. There are exceptions like Omaze where you are donating to a cause and receiving entires in return. Please look into your country’s respective tax laws for sweepstakes winnings. Depending on where you live, you may need to claim your winnings as taxable income.
  • Enter local contests. There is going to be a smaller pool of applicants for these vs. HGTV’s Dream Home Sweepstakes. You can find these in their email newsletters, their instagram pages, and posted at their physical locations. One of my favorite prizes was a local Goodwill contest where you had to find an NHL branded hockey puck within the store. Then when you found a puck, you were entered into a drawing. I ended up winning 4 tickets to a hockey game, 2 rooms at the team hotel, AND a $2000 Visa card to cover any other expenses. Local contests rock. 
Is “Sweeping” a Viable Side Hustle?

Why take my advice? I like to think I’m pretty lucky. But maybe it isn’t all luck. Maybe I just follow my own list of tips/tricks to win and they work. Here’s a short list of things that I’ve won. 

  • *Best Prize I’ve Ever Won* The prize mentioned above for 4 NHL tickets to an away game, 2 rooms at the team hotel, and $2000 on a Visa gift card. 
  • Concert tickets (I really focused my efforts here…since I realized I cracked the code on winning these). I won so many concert tickets that I was giving them away to friends. 
    • Blind Melon (my first memorable contest win)
    • The Used & Glassjaw
    • Jimmy Eat World 
    • The Bleachers & Bishop Briggs
    • New Found Glory (can you see a trend? I really enjoyed winning tickets to bands I enjoyed during my high school emo girl days)
    • Ghostface Killah – threw you off there, didn’t I?
    • X Ambassadors
    • Franz Ferdinand
    • Steve Aoki
    • Stone Sour
    • Walk the Moon
    • Galantis
    • Eli Young Band
    • Andrew WK
    • Milky Chance
    • Lucky Boys Confusion
    • Catfish and the Bottlemen
    • Reel Big Fish & Anti-Flag
    • Martin Garrix
    • The Orwells
    • Tchami
    • Zomboy & Stellar Spark
    • Q101 Sound Lounge Tickets – the room only holds maybe 20-30 people. The band puts on an intimate acoustic set. It’s amazing.
      1. Misterwives
      2. Nathaniel Rateliff & The Night Sweats
    • 2 tickets to a Sofar show. This was a Virgin Mobile Sofar show at a “secret location” announced just before the show. So fun and super cool. 
  • Yeti Tumbler 
  • $300 laser hair removal voucher
  • Free food! Most recently I won a Free Shawarma Wrap from a local restaurant. 
  • Tickets to the Waterpark
  • Tickets to the Maritime Museum of San Diego
  • Buffalo Wild Wings $70 gift card

So is this a reliable side hustle to pay off debt with? No. But…who knows, with these tips and tricks you might just land a big cash prize to pay off your Target bill. Or you might just get some free Shawarma and have a nice dinner. And again, “you can’t win if you don’t play”.

And to leave you with some additional terrible dad-advice, “you can cook an entire chicken in a wok in 2 minutes. You got 2 woks and 2 chickens? Still, only 2 minutes”. Good luck on all your sweepstakes entires. 🙂

1 comments on “Is entering Sweepstakes and Contests a debt payoff strategy?”

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