Yes, people actually win sweepstakes. I have won 163 of them over the last 20 years, from a $1.53 biscuit at Hardee’s to a $10,000 gift certificate. Here is the for real part though. I do not do it for the money. If I worked out my hourly rate on those wins, I would have to lie down. I do it because it makes me walk around feeling like something amazing could happen at any minute. That feeling is the real prize. The wins are a bonus.
I keep a record of every win in a little database. When I added them up to write this post, the number surprised even me. Not because any single prize was life-changing, but because of what the pile of them says. Two decades (with a lot of breaks) of hitting one button, mailing one envelope, filling one form. None of it felt like much in the moment. Stacked up, it tells a story about how I like to move through my days, expecting good things to find me.
Do people actually win sweepstakes? My 20-year scoreboard
Here is the real list, pulled straight from my records. Biggest at the top, with a sense of how far down the rest go.
| Prize | Year | Value |
|---|---|---|
| $10,000 Van Dyke’s Restorers gift certificate | 2007 | $10,000 |
| NASCAR weekend in Atlanta, Jeff Gordon package | 2005 | $5,000 |
| Sports dream package trip | 2005 | $5,000 |
| Royal Ceramic Club NFT | 2021 | $500 |
| Peroni designer bar cart | 2021 | $300 |
| Griddle grill | 2020 | $300 |
| Yeti Hopper Flip 12 cooler | 2017 | $280 |
| Nintendo Wii | 2008 | $250 |
| Two iPods | 2007, 2008 | $250 each |
| …and 154 more wins | 2005–2026 | $1 to $225 |
The smallest win in the database is a free candy coupon worth a dollar. Right next to it sits a $1.53 cinnamon biscuit, a $1.88 order of small fries, and more $5 Dunkin gift cards than I can count. The wins range from a single dollar to ten thousand of them, and that spread is a big part of why I want to be honest with you about what this is.
Why I do not count sweepstakes as income, and you should not either
Let me kill one idea before it takes root. This is not a side hustle. It is not a money strategy. If you divided my $27,000 in total wins by the hours I have spent entering over 20 years, the hourly rate would be genuinely horrifying. Stamps cost money. Time costs more. Most of what I win is a snack-sized gift card.
So please do not read this and think I’m suggesting it’s a clever way to make money. I am not, and I don’t consider it one. I enter sweepstakes for one reason, and it is the only good reason to do it. It is fun. It lights me up. If it did not, the math would have talked me out of it a long time ago. I’ve also taken many breaks from the hobby over the years.
That is my one rule for anyone curious about this. Only do it if you enjoy the doing, not because you are chasing the prize. The prize is rare. The fun is available every single day.
Why almost all my wins were small, and why I do not mind
Of my 163 wins, 119 were worth under $50. That is more than 7 in 10. Three wins crossed a thousand dollars. The rest were biscuits and gift cards and the occasional cooler.
If you are in this for the payout, the small ones look like noise. To me they are the whole point. Every $5 gift card and free snack coupon is a tiny reminder that I put myself out there and something came back. The win is not the gift card. The win is the little jolt of “no way, I actually got something.” A $1.53 biscuit can give me that as easily as a $10,000 prize. The small wins keep the feeling alive between the big ones, and the feeling is what I am here for.
The feeling I am actually chasing
My grandma caught an Oprah episode about everyday people winning sweepstakes when I was in my late teens. She called me before it was even over because she knew it would be my thing. I went all in. Decorated entry envelopes, stacks of index cards, mailing things off constantly. I won trips and electronics and bags of random swag, and somewhere in there I caught a feeling I have never shaken.
It is the sense that the next envelope, the next email, the next ordinary Tuesday might hand me something wonderful. That flutter on the walk to the mailbox. Thirty years later it is still there. I believe a little in the woo of it too, that holding that expectant, hopeful energy quietly invites more good things toward you. But I do not need to prove that to keep doing it. The expectancy alone makes my regular days feel lighter, and that is enough.
That is what entering gives me. Not prizes. A posture. I walk around a little more open, a little more curious, a little more sure that something good could be on its way. Expectant people notice more open doors, if only because they are actually looking for them.
How to win sweepstakes, if it sounds like your kind of fun
If that feeling appeals to you, here is the whole method. There is nothing clever about it.
- Enter the free ones, often. Plenty of sweepstakes let you enter daily. The free daily-entry ones are your bread and butter. No purchase, one form, every day you remember.
- Enter the small stuff too. The $5 gift card sweep has far fewer entrants than the dream-vacation one. Smaller prizes win more often, which means more of those little jolts of delight.
- Keep a simple list so you actually follow through. I track mine in a basic database, but a notes app works. The point is removing the part where you forget.
- Use the mail-in option when it exists. Most sweepstakes have a no-purchase-necessary path, usually a postcard. Fewer people bother, which nudges the odds your way.
- Stop the second it feels like a chore. This is the most important one. The day entering turns into homework, you have lost the only thing that made it worth doing. Walk away with zero guilt.
Today’s action
- Pick one thing that gives you that “something good might happen” flutter and do it today. A free sweepstakes counts. So does anything else that feels like a fun, low-stakes maybe.
- If sweepstakes are your thing, enter one free one in under five minutes and start a short running list.
- Notice the feeling afterward. Pretend like you already won it. That little lift is the actual prize, and it is the part you can have every day.
This is not actually about sweepstakes
Here is the part for you, even if you never enter a single giveaway.
Sweepstakes are just my favorite way of practicing something bigger. The habit of placing small, fun, no-pressure bets keeps me living in possibility. You cannot win a prize you did not enter, and you cannot be surprised by a life you never put any hopeful little maybes into. The pitch you almost send. The class you have been eyeing. The long-shot application, the silly contest, the idea you assume will go nowhere.
Most of those return nothing, the same way most of my entries do. That is fine. You are not doing it for the hit rate. You are doing it to stay the kind of person who keeps an eye out for good things, because that person has more fun and tends to catch more of them. Find your own version of the walk to the mailbox. If you want help sorting which hopeful maybes are worth planting, I made a seeds to plant tool for exactly that, and I wrote more about the mindset in how to grow your own luck one small action at a time.
Frequently asked questions
Do people actually win sweepstakes, or are they rigged?
People actually win them, and legitimate sweepstakes are not rigged. I have 163 real wins to prove the first part. The wins lean small because those sweepstakes get fewer entries, so the big ones are rare but real. Stick to sweepstakes with clear official rules and a named sponsor, and skip anything asking for payment to claim a prize.
Is entering sweepstakes worth your time?
Only if you enjoy the act of entering itself. As a way to make money it is a terrible use of time, and the hourly rate would be embarrassing. As a hobby that keeps you feeling hopeful and gives you the occasional jolt of delight, it can be well worth it. Judge it like a hobby, not an income stream.
How do some people win so many sweepstakes?
They enter far more than everyone else, and they keep a system so they do not forget. There is no trick beyond volume and consistency. The people who win dozens of prizes a year are not luckier than you, they have simply turned entering into a small daily habit they enjoy.
Why bother if most of the prizes are tiny?
Because the tiny prizes still deliver the feeling, and the feeling is the point. More than 7 in 10 of my wins were under $50, and each one gave me the same little lift of surprise. If you only value the big payouts, you will quit before one ever lands. If you enjoy the small wins, you get rewarded constantly.
Can you actually create your own luck?
To a real degree, yes. Luck is partly random, but how often you put yourself in luck’s path is yours to control. Every entry, pitch, and hopeful little bet is a fresh chance for something good to land. You cannot guarantee the outcome, but you can absolutely raise how many chances you give it, and stay more open while you wait.
People actually win sweepstakes, but the prizes were never the reason I kept going. The reason is the way it makes me walk around expecting something good. Find your own version of that, big or tiny, and do it because it lights you up. The wins, if they come, are just the bonus.
