In pursuit of financial independence and personal fulfillment

My wife’s a big winner (and you could be, too)

My wife has an uncanny knack for winning prizes. Not the land-a-ring-on-the-bottle-and-win-a-giant-bear kind of prizes, but more like the enter-to-win kind. To be honest, it’s gotten to the point where we just expect to win something anymore.

Last year, we entered a drawing in a small vacation town where we walked around to all the businesses and looked at their homemade gingerbread houses. If you got all the businesses to initial your ballot and then voted for your top three, you were put in the prize drawing. A week later, I got a call saying I had won a gift certificate to one of the restaurants in town.

I thought that was pretty cool. Then I got a text from my wife: “Guess who’s the grand prize winner!”

She won a free stay at a hotel, two other restaurant gift certificates, and two passes to a local attraction. It was about a $200 value, all told, and we won it for spending an hour walking around town admiring gingerbread houses. She also won a restaurant gift certificate for the same thing six or seven years prior.

In December, she went to her dentist for a checkup. They suggested a new filling, which she came back for, and they told her if she wrote an online review she would be entered into a drawing for an iPad mini. Last week, she went back for another filling (spaced out to maximize insurance) and they told her she won. Sure enough, she’s got a brand new $400 iPad Mini 4 just for spending 15 minutes writing a comprehensive review of her dentist.

At our annual HOA meeting, the first raffle ticket called for the grand prize went unclaimed, so naturally they called our ticket. We left with a pair of Utah Jazz tickets, a really nice Yeti mug, two hoodies, an emergency blanket and a high-quality Ogio backpack. That had to be at least a $100 value.

The reward for healthy living was a $130 FitBit.

In October, she participated in a monthlong healthy living challenge, turned in her tracker sheet and won a FitBit, another $130.

I think the reason my wife has been so successful with these is that she puts in the effort to do what it takes to get in the mix.

She didn’t have to walk around town looking at gingerbread houses. She didn’t have to write a thorough review of her dentist. She didn’t have to go to the annual HOA meeting. She didn’t have to do the healthy living challenge. But she did, and for that she got over $800 of things we actually use.

I know it’s cliche, but someone is going to win, and it might as well be you. But you can’t win if you don’t enter.


  1. CashflowKat

    Oh no, I’m here to tell you that you are wrong…your wife has the Midas touch and you better just be glad you hitched yourself to that wagon! I’ve entered everything under the sun and I can’t even win a cake walk at the school carnival! Haha, oh well…

    • I Dream of FIRE

      Those school carnivals are rigged, I tell ya!

  2. Steveark

    I was playing a tennis tournament late last year and one evening for entertainment we got to take turns each hitting a tennis ball across the court which was covered with mostly small prizes like tee shirts and warm up jackets but which also had a few buckets. If your ball landed in and stayed in a bucket then you were in a draw off with anyone else in the bucket for one of the big prizes. Six of us were in the bucket for an electric outdoor smoker/cooker and I won the drawing and was able to exchange the smoker for $300 credit at Academy Sports! The only catch was it was nearly closing time when I got to the store and they said I had to make the exchange right then and anything I didn’t spend it on I lost! It is kind of crazy hard for a frugal guy to spend $300 in thirty minutes, I was agonizing on getting the most value on things we would have to buy later anyway. It was kind of hilarious how hard I worked to spend that “free” money. At least I laugh about it now but it was even harder than spending my own money for some reason.

    • I Dream of FIRE

      Oh man that’s pressure! That would actually be a fun game show in a way, like a Supermarket Sweep.

  3. Rich Uncle EL

    Cool prizes and you have to be in it to win it. She is a real life lucky charm hold on to her she is a winner. LOL Good luck on the FI journey and your prizes.

    • I Dream of FIRE

      Absolutely. I ought to let her buy the lottery tickets next time!

  4. lisa

    I wanted to go to be a massage therapist and the school was giving a $10,000 scholarship if an essay was written on what area you want to specialize in for massage. I won. I was working full-time and caring for 2 kids. It didn’t cover the full tuition either. I couldn’t go for it . Bummer.
    I have won a pull wagon, lottery, auctions and recently, a online make-up giveaway.
    It’s fun and can be free. Nice to see people win something!

  5. [HCF]

    It seems you have a shamrock over there. Keep her safe, because it is not a common thing. For most of us winning a serious prize is a one-time event. Once I have won a weekend stay at a luxury SPA center, so don’t really expect anything soon, maybe in the next century 🙂

    • I Dream of FIRE

      Maybe it’s the smaller prizes, and therefore smaller number of people in the drawing, that make the difference? We certainly haven’t won the Powerball, but the smaller rewards add up!

  6. Indexia

    So Lucky man!! Really she is gem for you.
    Only few deserves such prizes. Hats off to her.

  7. Whymances

    I used to always hear about contests on the radio or local paper for concert tickets and wouldn’t bother with it. I usually never won and I was sure tons of people entered. When I started dating my current partner, it was a revelation how many tickets he’d win simply by entering. Sometimes it’s a numbers game and not as many people as you think bother with it.

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