My Worst Money Mistakes

My Worst Money Mistakes - picture of vacuum cleaner moving across the floor

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One of my favorite things to do is make fun of myself, and it’s partly because I make it so darn easy.

After all, I provide an endless stream of fodder for my own jokes, like the fact that I wear pajamas every day, all day.  Or the many times I have gotten drunk and performed tragic reenactments of my favorite songs during karaoke.  Or the time I texted my old boss and her husband with the simple words, “love you,” because I mistakenly thought I was texting Greg.


My Worst Money Mistakes

Well, today I thought I would share some of my most embarrassing and worst money mistakes.  You know, the kind you look back on and wonder what in the world you were thinking.  I’ve made great strides in my financial life over the past few years, but I haven’t always made decisions that were in my best interest.  Want to know more about my worst money mistakes?  Keep reading, because I’m about to spill the beans:

Buying a Brand New Car…with No Money

Dumbest Decision Ever
Dumbest Decision Ever

Just the other day, I wrote about the fact that so many people actually choose to be car poor.  Unfortunately, I have first-hand experience with giant, soul-crushing car mini-mortgages.  When I was in my early 20’s, I financed around $25,000 to buy a brand new Mitsubishi Galant.  Even worse, my job at the time only paid around $8 an hour.

I’m not sure what I was thinking, or how I even expected to pay such a huge car loan back.  I do know that my payments were somewhere around $500 per month and that they consumed half of my income or more at times.  Fortunately, I hunkered down and paid my car loan off as quickly as possible.  I believe the experience is what led me to seriously despise car payments, and vow not to ever have one again.

Financing a $1,300 Vaccuum

One day I was minding my own business at home when a door-to-door vacuum salesman offered to do a free demonstration and even shampoo the carpet in my living room.  I must’ve been bored because it sounded like a great idea at the time.  Over the next few hours, however, I started to fall in love with the Kirby Sentria vacuum and all of its various attachments.  Even though I hadn’t planned on it, I chose to buy it once his demonstration was over with.  Even worse, I financed it!  Yes, I swear.  And it wasn’t because I didn’t have the money.  It just seemed like the right thing to do at the time.  (Sad face)

And yes, I still have it.  Keeping it and using it forever is the only way I can justify the purchase.

Paying For a Disgusting Habit

These days, I literally want to vomit whenever I smell cigarette smoke.  Seriously.  In fact, I can’t be friends with you if you smoke.  Nothing personal.  But, back in the day?  I thought that smoking was awesome.  It helped me stay thin (or so I thought) and made me feel like a real adult.

Keep in mind, this was over ten years ago, so it was long before the days of electronic cigarettes that are more affordable.  It’s hard to estimate how much I paid for cigarettes over time, but I would guess it was at least several thousand dollars.  Yuck!

Failing to Track Our Spending

As we all know, it doesn’t matter how much money you make if you spend it all.  Unfortunately, we spent far too many years spending lavishly on home upgrades, toys, fancy foods, and stuff.  It wasn’t until we began tracking our spending that we realized we were spending over $1,000 per month on food for three people.  Yes, I’m serious. 

Not tracking our spending was one of our biggest money mistakes because it allowed us to lose track of reality.  Since we didn’t know how much money we were wasting, we didn’t stress out about it at all.  In fact, we personified the statement, “Ignorance is bliss.”

Well, guess what.  It isn’t.

Recovering From My Worst Money Mistakes

I’m happy to be a reformed spender, and I’m glad that I no longer have to be the victim of my own bad decisions.  However, it’s still fun to look back and see just how far we’ve come.  At least now I can look back and shake my head at my crazy antics, knowing that we’ve done so well since we changed our ways.  And the good news is, no matter how bad your worst money mistakes are, it’s never too late to change.

What are some of your worst money mistakes?  Do you find them funny now?

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  1. Probably our biggest money mistake was living like rock stars on student loans. We paid for all of our living expenses and them some when we were living on student loans. We even took a trip to Mexico courtesy of our loans! Ugh, and we are still paying for these mistakes, as we are still working hard to pay off our student loans.

    1. So many people have done the same. That sucks but you live, you learn!

  2. I’ve been guilty (obviously) of the whole car payment thing, and now it’s going to take s forever to get away from it. However, my biggest regret is all of the time I wasted “creating” a budget, but not really getting anything useful from it. Setting unrealistic budgets, not sticking to budgets, and not thinking ahead and budgeting for expenses that varied month to month.

  3. I think my worst money mistake was not paying off my student loans quicker. I just made the minimum payments, even when I could have easily paid more.

    1. We paid the minimum payment on Greg’s loans for years.

  4. Haha I actually have a friend who was a vacuum salesman when he was 18. He made a TON of money selling $3,000 vacuums. It was crazy and I never understood why someone would pay so much money for a VACUUM!

    1. Now you know!!! It really is a nice vacuum! Haha!

  5. I didn’t realize vacuum salesman actually existed outside of movies haha. Amd really if you get a good long use out of it then really its more of an investment. I’ve probably spent like $600 om shitty vacuums bc they die. And good for you for quitting smoking. So gross.

    1. Smoking is so gross. I can’t believe I smoked.

  6. My dad has some great stories like these– things that you look back on and think “how could you even think this way”? Like the time he sold his house with two acres of land in a very nice area, and when the buyers (after the contract had been signed) asked if his other 1.5 acres was for sale next door he said “you know what, I’ll just include that with the house!” He still looks nauseous every time it comes up.

  7. Yep I’m guilty of not tracking our expenses in the past. Now that we have Quicken, I track every penny, in every account, every day. We weren’t spending 1k but we were really overspending on food.

    1. It’s easy to do. We never tracked it but we thought we were doing good when we bought groceries instead of going out to eat.

  8. “Love you.” ….such nice drunk texts. I can imagine what could have been texted….that could have been ugly.

    Car salesmen are frustrating. You were oversold a car and learned your lesson. Had he/she talked you into a more reasonable car, you might be still financing cars today. Better for you that they let you go off the deep end, huh?

    1. That’s true. That car payment seriously impeded my ability to move ahead in life in my early 20’s. I think it scarred me for life against big car payments!

  9. I never really smoked cigarettes, but I did smoke cigars and I look back now and wonder what on earth I was thinking. Anyway, I didn’t have any huge money mistakes…in terms of dollar amount. Mine was just a bunch of stupid stuff I had no business buying. My worst one was probably funding trips to Vegas on my credit card just because.

    1. I have done a lot of small, silly things too. I used to go shopping on credit just for the fun of it.

  10. Car and TV…yes, my very first TV in my 20’s was purchased on one of those “pay zero interest for one year” type deals…I SO did not pay it off in time. 🙂

  11. I think the biggest mistake I’ve made, the one that still gives me a stomach ache, is how I borrowed so much in student loans without a real understanding or plan for paying them back. I just assumed I’d make big money and it wouldn’t be an issue.

  12. That’s “love you” text is awesome!

    I guess my biggest mistake would be buying a motorcycle… and I only say that because I am not riding it anymore and haven’t sold it yet. I don’t regret buying it, it just doesn’t make sense to ride now that I have kid(s).

    1. I know A LOT of people who sold a motorcycle after having kids. There just isn’t as much time to go riding anymore!

  13. OMGosh the vacuum. I had no idea they made vacuums so expensive. Does it do your dishes? 🙂 heh heh. Hey, I have no room to talk. I think one of the biggest money mistakes was signing up for life coaching classes (using my credit card) while freelancing but not tracking my spending and not bring in much money at all. I hate when “experts” give advice to people who may be in debt or have a family to support that “now” is the best time to quit their miserable jobs and peruse their passion. I think that advice is crazy. But that’s just my thought. Other than that was my run of the mill credit card spending. I don’t look back and laugh at all, but I also don’t beat myself up too much. We all make mistakes.

    1. It is a really nice vacuum and I love it! Totally not worth $1,300, but there is nothing I can do about it now except keep it forever!

  14. The vacuum one made me chuckle at my desk! I just went in on a $400 Dyson vacuum for my friends’ wedding. That seemed like such an absurd price for a vacuum that $1300 almost made me choke on my water!

    1. Yeah. Well, it’s a carpet shampooer, multi-tool too. It’s pretty badass- I have some super clean floors, baseboards, and vents!

  15. Ha! The vacuum one cracks me up. When I was younger I financed a car too. I worked 2 jobs while in school to pay it off. Never again!

    1. Yep, same here. That car payment killed me for so long.

  16. OMG! I love the vacuum story. We had the demo as well, but refused to pay that price. About 2 years later, one of my neighbors put and selling their Kirby, for $125!!!! I ran over there and purchased it. Had been used like twice, everything complete. We found the papers with invoice, the hubby had financed it $1795!!! I don’t think the wife ever knew cos she wouldn’t have sold it that cheaply. It is a great vacuum, good news is most cleaning companies use it and you could still sell it for good money. We left ours with the neighbor. If we move back, l want it back. I’ve made the car mistake, the credit card mistake, the motorcycles mistake etc..etc..etc.. ;o)

    1. Yep, I’ve made lots of mistakes. Too many to list in a blog post.

  17. My biggest one was financing a JetSki on a promotion. That was so stupid and it cost me so much. Low and behold it broke down a few years later and we only used it about 10 times. Worst purchase ever!

  18. My first summer job was as a door to door salesman. I was a Fuller Brush dealer. I earned enough that summer for my college spending money. It was a great experience, but no financing!

    I have had my share of money mistakes, but the only one that bothers me is when I sold Amgen at $45. It has split many times and currently selling at $119.

    1. Ugh! Oh well. You could’ve lost big too. Hindsight is 20/20~

  19. Ha! I love the text you sent to your old boss. I once sent a wacky drunk text to my father in law because he and my hubby have the same name. For me, the worst money mistake I ever made was not tracking spending and not planning larger purchases more. It is amazing how many mistakes you will make when you don’t pay attention. I also had a habit of buying large items and not figure out how I was going to pay for them until after the fact. I am glad to be a reformed spender as well. 🙂

  20. I think our worst mistake was putting a new car purchase on our home equity line of credit so we could deduct the interest on our taxes. We traded the vehicle before it was paid off so of course the balance had to be rolled into the next loan. I think we paid for that car at least twice before the loan was gone.

    1. Yikes! I’m sure it sounded like a good idea at the time =(

  21. Oh the vacuum! I love vacuums so I totally understand why you were tempted! They’re just so awesome with all their cute little attachments and hoses :).

    I think our worst mistake was a weekly restaurant trip for years–we went out to eat every Saturday night. I hate to think about how much money we could’ve saved!

    1. It really is a nice vacuum. Not worth $1,300…but still….

  22. I think my worst money mistake was not getting an emergency fund set up ASAP after graduating college and starting a job. At the very least I could be moving $100/month into it. Instead I just kept my checking which, as I’m sure we all know, is much easier to spend than a designated “emergency” fund that you only touch if you absolutely have to.

  23. What? No video of your karoke performance? That must have been one amazing sales pitch for that vacuum cleaning!

    1. I would probably fork over my life savings if anyone tried to bribe me with a video.

  24. Hey Holly, thanks for sharing your worst money mistakes. Definitely fun to read! I think the worst mistake I’ve made with money is drinking it away in my early 20’s. Unlike most 21 and 22 year olds, I had one heck of a salary. So, I would invite my friends to the bar and when they couldn’t afford it, I’d offer to pay….dummy! Anyway, I’m not a stingy person, but I’m definitely not spending 30k in a year buying friends drinks anymore.

    1. Oh yeah. I spent way too much on alcohol in my early 20s!

  25. Holly, I have that same vacuum. Still using it too because it was the most dumb thing I ever financed. I sent a text recently that was supposed to say “just read the last part” but it somehow got sent as “bread the lady part.”

  26. My mistakes have been: financing every car I’ve owned; living off my credit cards; living off my overdraft; financing a computer; not having any savings. Oh the list is endless…

  27. I’m glad the vacuum cleaner is at least a good one! My dad purchased a Dyson for my mom one Christmas and I couldn’t believe the price, but she loves it. One of my worst mistakes was probably buying my bed and not negotiating. It was on sale for what I thought was a decent price, but I didn’t have much knowledge of the mattress industry back then, and didn’t realize how much markup there is!

  28. Dear God I have too many mistakes I’ve made to list! I leased a brand new car Pontiac Sunfire fully loaded at 18, moving out at 21 and then scampering right back home to mom because I wasn’t able to manage the rent…I could go on and on. Kudos to us for sobering up financially!

  29. I can forgive you for everything you mentioned… Everything except your choice of vehicle. Seriously, a Mitsubishi??? 🙂

    My worst money mistake was not knowing a good money mentor. You know, somebody like an elder who knew about stock market, real estate and small business investments. I had to learn about each area on my own.

    1. I didn’t have a money mentor either, but now that we’re becoming money and market wise, I think it’s important to pass that information along. I just got back from a family party and brought up retirement plan to my brother in law because I know they’re a mess financially. I got a dumb answer “my work figures that out for me” Then dropped it because I knew he didn’t want to talk about it.

      I try not to push it but you every once in a while you’ll get people that will ask follow up questions and you can talk about the 4%/25x rule and a quick talk about why you want boring index stocks and the power of compounding interest. I haven’t found a single person around me that has ever heard of these theories. You just gave them a goal they can easily figure out with the 4% rule and how to do it with compounding interest in index funds. You may just spark something in them to do further research and change their life.

  30. Ugh! I hate door to door sales people coming around my house especially at dinner time. I had to buy a No Solicitors sign and put it on my front door! Anyway, not tracking my spending is one of my money mistakes as well. I’ve learned that lesson now but I think it’s a very common mistake.

  31. $1,300 for a vacuum cleaner? That’s pretty insane! Does it also make ice cream for when you’re sad? :)))

    I used to smoke too and I am happy I managed to quit 6 or 7 years ago. I know that when I did, I calculated the average price for a pack of cigarettes and estimated how much I had spent over the 10 years I used to smoke. It was a bit over the price of a decent second hand car. So maybe smoking is one of the reasons why we get car poor, too :))

  32. I guess my biggest money mistake is my student loan, but I still see that as an investment. I also went overboard buying nice things for my apartment, even though I was planning to leave. It’s really frustrating now looking to give away or sell my stuff, ugh!

  33. I did the car finance thing. Once was enough…never again. Then I drove that car into a parked RV when I was driving into the Arizona sun…I was blinded and by the time I saw it, I swerved, but it was too late. That stupid car landed me in two financial messes…

  34. That vacuum will last a LONG time. My mom had her Kirby for over 20 years (I can remember the salesman demoing it at our house when I was 4 or 5) , and recently replaced it with a newer model. I don’t consider that a silly purchase, just sticker shock for QUALITY that won’t break (and has service centers if it does) after a couple years of use. Quality of a product is definitely worth the investment!

    1. Ha! I actually love he vacuum. It is works awesome. The rest of the vacuums we had died after a year or two.

      1. I keep hearing about vacuums having a life span of about 2 years. Everyone is in disbelief but 10 years later I still use my $40 Eurika I bought when I was a freshman in college in my first apartment. It gets heavy use today with 2 cats and a dog and the whole house is carpeted. I just give it a thorough cleaning every couple months and clean out or replace the filter. Might have just gotten super lucky.

  35. Lisa E. @ Lisa vs. the Loans says:

    “Mini mortgages” – car loans really do feel like that! My current car was bought brand new and I absolutely hate every time it’s time to pay that bill! Can’t wait to get rid of it.

  36. My biggest mistake was not understanding very early on that if I just lived a frugal lifestyle, that I could actually retire at 42 and only do the things that I wanted to do after that. Now I’m making up for that mistake as best (and as fast) as I can!

  37. I have two.
    1. We decided that our daughter needed a 4-wheeler. We lived in the city but we could take it up when we visited the in laws. My husband said that we should also buy one for our youngest daughter too. So we financed 2 4-wheelers to the tune of about $4,000. The baby hated it and barely rode it. The oldest daughter rode her maybe 5 times because we didn’t have anywhere to ride them. Sold them 5 or 6 years later for way less than 1/2 what we paid for them.

    2. Bought a beautiful old Bronco for a used car lot. It was big and green. Just $9,000 worth of gorgeous. We used our home equity line and bought it. We had to have it. Less than 6 months later the gas prices shot up so high we couldn’t afford to drive it. Put it up for sale. No one else could afford the gas in it either. So it sat – and started to rust. Sigh!!!
    We used it as a trade in on a new car. I don’t remember how much they gave us but it wasn’t anywhere near the $9,000 that I am sure we had not paid off yet.

  38. I’m still guilty of not tracking our spending — until about a week ago. I finally signed up for Mint and am familiarizing myself with the software and its capabilities. I bet my husband and I spend WAY MORE on food than we should, and I’m interested to learn just how much more. I was also dubbed into buying $60 worth of magazine subscriptions from some dude on campus…worst. feeling. ever.

  39. Buying pricey vacuums is a no no. Thanks for sharing this blog it is quite entertaining. I am also guilty of many financial mistakes, especially on car loans.

  40. I came home one day last year to my girlfriend getting a sales pitch for a Kirby vacuum, I think they wanted like $2500 for it, no joke. Took a good amount of restraint to not throw him out the door with force immediately. I held my breath I was kind, I even let him do a bit of spiel and then I let him down and told him he was really wasting his time and he left. Tried to sympathize and say I know it must be hard to sell such an expensive item. I assumed it was an average product, only later did I realize it really is top notch, but according to Consumer Reports you can get just as good vacuums for under $200 bucks.
    I also seriously thought about buying a new car last year, but it would’ve been a work car with many miles reimbursed. I ended up dropping the new car idea when my boss said they want me to use the company vehicle whenever it’s available, which is pretty frequently.

    I once bought a $6000 motorcycle on a high interest loan when I was in college then lost my job a few months later. I got by freelancing computer work but it was extremely frustrating seeing $110 of my $150 payment go to interest. That was a big lesson for me in loan interest rates. Took me 8 years later to finally wise up, I’m only now currently trying to sell that same motorcycle.

  41. I have made many financial mistakes in the past, until I realized that tracking my spending helped a lot to avoid unnecessary expenses. I use a simple Excel sheet.

  42. … and before buying something ask yourself: do I really need it? Why spend your hard-earned money on something that will just sit in a closet? Avoid buying something on impulse.

  43. I’ve had the Kirby salesmen come by several times. I normally let them in because I feel sorry for them since they’ve normally been hoodwinked into that “job.” I’ve had one salesman just look at me after his manager left and say “you’re not interested in this at all, are you?” to which I replied “no.” So we just talked until his manager came back and pretended he did the sales presentation so he could get his little bit of compensation.

    Another time I had a salesman get real aggressive, except that his main selling point was that if I bought his vacuum he could go to the Bahamas! That guy kind of made me made.

    Oh, and there was the time my Dyson outperformed the Kirby…. Granted, the Dyson is a $600 vacuum, but still far cheaper than a Kirby.

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