The Best $20 I Ever Spent

winning raffle ticketIt was March 2012. We were just under the half way point in paying off our $30,000 of credit card debt. While we were feeling pretty good about our progress, we still needed to be careful about every purchase. Each penny spent was a penny that wasn’t going toward getting us out of debt. I don’t remember the exact date, but I made a decision that day to spend some money, and it turned out to be the best $20 I ever spent.

What Did You Buy?

You probably expect me to say that I bought some self help book or magic vitamin that melted off all my cholesterol. Nope, I bought a raffle ticket. Generally, I think buying raffle or lottery tickets is the same as taking money to the toilet and flushing, but hear me out.

At the time, I was president of our area humane society. The local  homebuilder’s association had chosen us as the recipient of their fundraising drive at the annual home and garden show that year. They always have a raffle. It costs $20 for a pack of 5 tickets. First place was a huge flat screen TV. Just the thing every person on spending lockdown craves!

I didn’t really expect to win anything, but after two days in a booth at the show, I kind of felt like the association people were family. I decided my purchase was going to a good cause, and I bought a pack of tickets for $20.

Why Are You Calling My Name Over the Speakers?

At one point toward the end of the show, I was milling about and heard my name being called over the loudspeaker. I assumed it was a pet related issue at our booth. The main platform of our humane society is spay/neuter promotion, and beneath our logo, it says “Support Planned Pethood. “

Apparently, lots of people from our very conservative town can’t read because there were several attendees who were very angry that we were promoting Planned Parenthood. After I explained that we had nothing to do with human reproduction, we usually had a good chuckle, and it sometimes led to a donation. That’s what I thought was going on when I heard my name called.

Instead, I was pleasantly surprised to hear that I’d won the raffle!

How Am I Going to Get My New TV Home?

I was considering how to fit my new, giant TV in the car when I found out that I had actually won 2nd place, not the grand prize. After a brief second of disappointment, I was given my prize, which was a brand new laptop! It was a bargain basement, off brand laptop that retails for under $300, but that was still a pretty good return on my $20 investment.

My New Laptop and a World of Possibilities

At the time we had a decent laptop, but Jim always  hogged needed to use it for work, and he was just starting an online master’s program. That left me about 5 minutes a day to use the internet. We weren’t about to buy a new computer until we were out of debt.

Now I had this new found bounty. What’s a motivated girl to do? Since I couldn’t very well start online shopping, I began devouring personal finance blogs. The more I read, the more I was in awe of people who were doing amazing things as far as paying off debt, using money wisely, and building wealth. Holy crap, there actually were people who retired early!

Up until that point, I felt very isolated from the real world because most of the real world lives in the cycle of monthly payments and debt. Finally, I found my people! After lurking for a couple of months, I started commenting on a few blogs. Then, I took the leap in July 2012 and bought the domain and hosting for Eyes on the Dollar, even though I knew next to nothing about online enterprises.

The Best $20 I Ever Spent

Without my $20 laptop, I would have never had any idea I could earn a five figure amount of money from online side hustles in just under 2 years.

If I hadn’t won that laptop, I’m sure our debt repayment would have been much slower or we might still be in debt. I would probably still not be maxing out my retirement account or my HSA. I am very sure my family would not be taking an almost free trip to Hawaii thanks to credit card churning. I am 100% sure I would never have thought it possible to reach financial independence before age 50, but that’s now a very real probability.

I am usually not a believer in fate or luck. I think most people make their own luck from how they view the world and what it throws at them. I don’t think everyone should go out a buy a raffle ticket in the hopes that it will change their lives. But I do think if you are given a gift, a stroke of fortune, something you can take as a sign, you should run with it and max it out for all it’s worth. That raffle ticket was the best $20 I ever spent.

Do you normally buy raffle tickets? Have you ever won a drawing?


Image: Wikipedia Commons

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Written By
Sydney White is a Texas-born stay at home mom who enjoys spending time with her family, bargain hunting and, of course, writing. She is currently the editor-in-chief of


  1. Love this, Kim! It just gives to show how being open to possibilities (and a little courage) can lead to great things. I admit when I started blogging that I had no idea what a wonderful community of fellow bloggers existed. And now that I think about it, I’ve given away prizes at raffles but I don’t think I’ve ever won anything big. 🙂 Have a great weekend!

  2. Hey Kim, I don’t ever buy raffle tickets, but I can definitely see how that was the best $20 you spent. I’m glad you did! You’ve got an awesome blog, and it seems like that $20 raffle has changed your life in amazing ways…gotta love the butterfly effect.

    1. Thanks! I almost never buy any sort of raffle ticket either. It was a fluke for sure, but a good one.

  3. I often think about how tiny little moments like that change everything. Be it winning a laptop or just waking up five minutes earlier to put you in the right place at the right time to seize a life changing opportunity.

    ps. I’m a HUGE planned parenthood supporter. For the five years I had no health insurance, it was the only place I could go to get regular check ups and pap smears for free.

    1. Sadly, those people who hate Planned Parenthood are also the ones who think welfare mothers are a blemish on society.

  4. That’s awesome! It must have been fate. I’ve won a couple blogger giveaways and I won a 500 gift card to a mall about two years ago (I used it mostly all on the grocery store attached to the mall-boring eh) so I’d like to think I’m somewhat lucky!

    1. I won a Suze Orman book and $25 in blogger contests. It’s exciting to win anything, and $500, even for groceries is awesome.

  5. I would say that is a very good investment. I typically don’t buy raffle tickets, but I will for a good cause. I have never won anything though. That is one reason why I don’t buy lottery tickets. My money apparently only comes from hard work. I don’t have the luck.

  6. Amazing story! You’ve come so far in that amount of time…and to think it was all from a raffle ticket that I think most personal finance geeks wouldn’t have even bought! I guess I didn’t realize that you have accomplished all of this (including the 5 figure income) in two years! That’s awesome!

  7. Great story! I’ve never won anything big from a lotto pr raffle ticket 🙁 I totally understand what you’re saying about the one computer thing though. My laptop is deadddd (it’s almost 8yrs old) and ive been relying on using my husband’s work computer when he’s done with it…which gives me little to no time to get stuff done (like this week me not being able to finish my posts….) so I have finally accepted that I need a new computer if im going to meet my freelance deadlines etc. i don’t plan on spending a fortune though…maybe $400…I’ll be glad to have freedom again 😉

    1. I could not blog if I didn’t have a dedicated computer, unless I gave up sleep completely and did blogging at 2AM.

  8. Wow, it’s amazing how such small little strokes of luck can snowball and become potentially life-changing when you make the most out of them! What a great story Kim!

    I very occasionally buy raffle / lottery tickets, but when I do, I realise that I’m simply paying for a little buzz of excitement, and nothing more. When you start expecting or relying on those things to change your life or make you rich, then you’re usually heading down a steep road to misery.

    But if I do ever have a similar stroke of luck, I’d like to think I’d be very grateful and max it out for all it’s worth 🙂

    1. I think most people who win something significant tend to blow it on stupid things. If lottery winners who blew all their money had just invested and continued to live within reason, I bet they would be so much happier.

  9. Great story Kim. I’m with you, I’d just as soon light $20 on fire as buy a lottery ticket, but if you’re donating to a good cause that’s a totally different issue. Glad you’re online! 🙂

    1. Thanks! I certainly thought I was just donating to the cause. Winning was a really nice surprise.

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