“I Won 50k in a Sweepstakes!”

vintage hersheys kisses poster

I thought that if I was ever going to get out of the debt I needed a miracle. The options I saw in front of me were to either file for bankruptcy or win the Lottery (and I didn’t even play the Lotto). I’m really curious about these two financial extremes (here’s the 1st interview). Throughout this series I will be interviewing people who have either filed for bankruptcy or who have come into very large sums of money through unconventional means.

We will be exploring the effects of both on life in the short and long-term. In the final installation of this series I will be interviewing a man who won 6 Million Dollars in the Colorado Lottery. I hope you find these interviews as interesting and insightful into the extremes of money as I do. 

The 2nd interview in the series is with a lovely lady named Jessie. She won 50K in a Sweepstakes. I’ll let her tell you the rest!

And Then We Saved: What year did you win and what is the total amount of money that you won?

Jessie: I won $50,000 in 2003.

ATWS: What is the name of the game you won? 

Jessie: Hershey’s Great American Dream (Second Chance Drawing).

ATWS: Can you describe how you found out that you won? What was that like?

Jessie: I was working for the university painting apartment buildings and dorm rooms during the summer. My roommate was also working with me and over the lunch hour she went home and said, “Jessie, your mom called and left several messages on the answering machine. You should call her back.” I blew it off as my mom just wanting to chat. When I got home after work that evening, I had SEVERAL more messages. I called my mom and she frantically told me the good news and read the letter I had received in the mail. I was in complete shock, and my mom was irritated with me for not calling her back all day.

ATWS: What was the 1st thing you bought?

Jessie: I had to wait several weeks until I actually received the money. In that time period, I thought about what I truly wanted/needed to buy. One thing I had wanted for awhile was Lasik eye surgery. I had worn glasses since first grade, so I found the best doctor in the state and scheduled my first appointment. The procedure was fairly new at this time and one of my eyes needed a special procedure, so it ended up costing me about $6,000. I never went on a “shopping spree”; instead, I focused more on large items that were a priority for me.

ATWS: How has your life changed and how has it stayed the same since you won?

Jessie: The win allowed me to pursue graduate school. If I hadn’t won, I probably would’ve been more conservative, taking a job after graduation. Because I was able to graduate from undergrad without any student loans, I took a leap of faith and pursued additional education. Other than that, I don’t believe my life changed.

ATWS: What is the biggest surprise that you encountered right after winning?

Jessie: I think I was afraid people would be judgmental or angry that I’d won and not them. In actuality, however, everyone who found out about the win was very supportive and happy for me. I never felt any hostility what-so-ever, so that was a surprise.

ATWS: Did you have an option to choose a lump sum option or an annuity? 

Jessie: I didn’t have an option. I had to take the lump sum.

ATWS: How do the taxes work with winning that amount of money? Was there anything that came up with the taxes that was a surprise?

Jessie: Money received in this way is considered “taxable income”. So the $50,000 was taxed just like the income I received painting that year. Overall about $12-13,000 went to taxes. I was a college student and not very familiar with taxes up to that point, so I was surprised (and sad) at the amount of money leaving my pocket.

ATWS: Did you have a financial planner/advisor or deal with your finances on your own?

Jessie: I went with my parents to speak with an accountant and a financial advisor after the win.

ATWS: How long had you been entering contests/sweepstakes at the time that you won?

Jessie: My mother had been entering sweepstakes and couponing since 1974. I guess she passed the bug onto me when I was born. When I was only 10 years old, the grocery store in my small town was giving away a children’s kitchenette. I would go to the grocery store with my parents and repeatedly enter the whole time I was in the store. I ended up winning the kitchen and that spiked my interest from then on.

ATWS: How did it come about that you entered this contest?

Jessie: Hershey’s was conducting a second chance drawing. Essentially, if no one claimed a winning candy bar wrapper, then they would draw for the money from the entries they received online. My mother discovered that if you entered this sweepstakes online you almost always won a coupon for a free Fast Break candy bar. So we entered everyday. Our downstairs freezer was full of Fast Break candy bars (they’re delicious)! We had a bunch of bars and a bunch of entries online.

ATWS: Did you have a feeling you would win big someday? If so, what gave you that feeling? Any way to describe it?

Jessie: No, I had a blessed and lucky life, but I was never expecting a win so great.

ATWS: Do you consider yourself lucky? Are you lucky in any other areas of life?

Jessie: Up until that point, I would have never considered myself “lucky” with regards to contests/sweepstakes. Now, after winning $50,000 I definitely consider myself lucky. After the win, I threw myself into entering sweepstakes, and I’ve had many successes. I don’t win something every day or every month, but occasionally a nice win comes along that makes it all worthwhile.

ATWS: Does anyone else in your family play sweepstakes/enter contests? Did you “inherit” this trait?

Jessie: I inherited this trait from my mother, without a doubt. This is one hobby we both have in common. She has also found a great deal of luck in entering sweepstakes.

ATWS: Have you won any other contests/sweepstakes? If so, what did you win and when?

Jessie: I have won too many sweepstakes to remember them all, and unfortunately I didn’t begin recording my wins until this last year. Some of my larger and more memorable wins include: a trip to Santa Monica (2008), a trip to Costa Rica (2011), a Sony Handycam camcorder, a down comforter from Oprah, a $1,000 check (2009), a nice golf bag, many different make-up, anti-wrinkle, nail polish and hair products. The strangest win I’ve ever received was a Vogue magazine with the cover encrusted in Swarovski crystals.

ATWS: How do you feel you have handled this big win? I’ve heard it can have adverse effects on some people/relationships… how did you avoid this and stay sane?

Jessie: I think I took a clear-headed approach to the win. When they discovered I had won, many people described the type(s) of vehicle they would have ran out and purchased if they had won. Even though my vehicle wasn’t glamorous, it was reliable; so I focused more on my education and my future. I bought a new computer, I paid for my schooling and I put some away in a Roth IRA. To me the money was already spent on my schooling, so I didn’t feel like I was walking around with a big chunk of money in my purse. This thinking kept me grounded (and frugal) in the long run.

ATWS: Was there a lot of press about your win after you won?

Jessie: Not really – they published articles about my win in my hometown newspaper, in a publication released at my undergraduate university and in a refunding magazine.

ATWS: Do you still enter sweepstakes/contests and do you think you might win again?

Jessie: YES, I still enter and YES, I believe I will win again!! I really hope my next win is a new car … I’ve been trying to win one for 8 years now, so I think it’s about time.

ATWS: How (and have?) your thoughts on work changed since winning?

Jessie: My thoughts on work were never affected by my win. I had worked since I was 14 years old and working was merely a part of life.

ATWS: What’s the most expensive thing you’ve purchased with the winnings?

Jessie: College – I know, I’m super boring.

ATWS: What’s the most common question that people ask you when they find out you won a large sum of money?

Jessie: They want to know how I won. They hear “Hershey’s” so they assume it was by eating a candy bar. It takes some explaining before they grasp how I actually won.

ATWS: Do you ever get sick of talking about it?

Jessie: No, I love entering sweepstakes. It’s a unique hobby and I hope to inspire others to enter.

ATWS: Do you think winning the money affected your short term happiness (directly after winning) and quality of life?

Jessie: Definitely – the win took a great deal of stress off my shoulders. Before the win, I was worried about making ends meet, but the money provided a security blanket for me. I was able to focus more on my studies and go grocery shopping whenever I needed to.

ATWS: Do you think winning the money has affected your long term happiness (today …years later) and quality of life?

Jessie: Yes, the win propelled me into entering sweepstakes more frequently. It became a hobby that I genuinely like to do – it adds to the happiness I already had in my life before the win.

ATWS: Do you have any debt?

Jessie: YES!! Eek! We have a mortgage, a car loan, and both my husband and I have student loans. Every month we try to pay extra principal towards each of our loans to help speed up the pay-off process.

ATWS: Do you try to keep it “under wraps” that you won such a large sum?

Jessie: Typically, yes. I usually only tell people who I feel comfortable around.

ATWS: Do people ask you for money once they find out that you won a bunch of money? What’s the strangest/most interesting request?

Jessie: I have yet to have someone seriously ask me for money. There were a lot of sarcastic requests for money right after the win.

ATWS: What would be your recommendation to anyone who wants to win contests and sweepstakes? Any secret insider tips on how to win BIG?

Jessie: If you have to pay money to enter a sweepstakes, then you’re doing something wrong. I only enter a sweepstakes if it is costing me nothing. If you want to win, you have to enter. It’s kind of like praying to win the lottery but never buying a ticket.


● Jessie, thank you for telling us all about your win. It’s exciting! Thank You for being a part of And Then We Saved.●


10 thoughts on ““I Won 50k in a Sweepstakes!”

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  1. Francesca

    I do like entering sweepstakes also, but lately have become so skeptical. Like at the mall, they have all those stands to win something, but the next few weeks after putting your name and info somewhere, the house gets all kinds of telemarketer calls. Or you get a call back stating you won, but the next thing, your being hounded for something else that cost money… I guess you have to be aware of the type of sweepstakes you enter. Good luck all!

  2. Anna Newell Jones

    I am a skeptic most the time too. The telemarketers, etc. are a major deterrent to entering & a crappy side-effect but I guess it pays off sometimes!

  3. Sarah

    Hard to read this! He has debt and didn’t pay it down with the $50K? It would be great to interview a financial advisor on the right way to handle a windfall.

    1. Anna Newell Jones Post author

      Hey Sarah, Sorry if it wasn’t clear (actually I probably need to look at that right now;) but she paid for a portion (approx 1/2) of law school with the winnings. She said she wouldn’t have gone to law school if she didn’t win. Even though they still have debt she’s able to make more with the JD.

  4. Venaswearengin

    I hope is me win I Really need it bad I pay off bill N other thing ask well no money to do anything sometime I feel like give up No I am going to keep going I beliveGod is good


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