Painful Financial Mistakes – Part 1


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There’s valuable stuff in hearing about people’s mistakes. So I thought I’d share some of the painful financial mistakes that have stuck with me. This will be a two-part post, and I’ll share Part 2 later this week.

2-Year Gym Membership

When I was entering my second year of college, I visited a friend’s gym because he had a membership and could take a friend for free. We asked about signing me in as a guest, and the muscle-bound guy helping us (late-30’s, definitely manager-level) looked at me, “Are you serious about looking into a membership or are you just coming in here for the free workout?”

I immediately felt guilt over the fact that I was definitely there for the free workout. I had zero intention of signing up for a membership. I felt like I was stealing from this guy and certainly like I was wasting his time. As a 19-year old, I was still very impressionable and cared a lot about what others, even complete strangers, thought of me. It also felt a bit like he was calling me a free-loader which made me want to show him that I could afford it.

So I did what any naive teen would do, I told him I was interested and he gladly signed me up. I think I went for a month, maybe two, and then never again. I tried a few times to get out of the contract, but failed. There were definitely a few times where I really needed that money, but it was a committed monthly spend, regardless of anything else.

Sure, I wish that I hadn’t signed up. But I learned a valuable lesson from it. I have never again signed up for some dumb contract, and I’ve been extremely cautious about being duped or guilted into buying something I know I don’t need.

Costs: $59 per month, 2 year contract = $1,416 (as a college student, this HURT!)

Buying Stuff New

It’s hard to quantify how much money I could have saved here. I didn’t realize that, for most of these items, I could easily find them used at yard sales or on craigslist. While I am an intense and strategic planner, I have never been all that “frugal”. It has something to do with not having to worry about money as an adult, thanks to a good paying job. My wife, on the other hand, was brought up by one of the most frugal people I’ve ever known (her mom). And, by contrast, my wife is a social worker.

Thankfully, she enlightened me during our first yard sale. I saw my $60 jeans going for $2, and my $60 video games going for $4. Brand new books I hadn’t had a chance to read yet going for a quarter.

Books: I still buy audio books, but I use an Audible subscription that gives me 30% off any book (plus one free book a month), as well as the ability to exchange a book if I don’t like it, even if I’m half-way through. I like that they are organized into a digital library so that I can listen to them over again periodically.

However, for paperbacks, I will check the library first to see if they have it. They generally do, and if not, I can find them used on Amazon for a good price.

Clothing: I’ve spent thousands of dollars on unnecessary clothing. Men’s clothes aren’t the easiest to find used. I just wish I hadn’t bought so many. I’d buy 10 pairs of jeans, but only really wear two or three of them often. I’d buy four to five pairs of shoes and have 20-30 shirts. This is an area that I now subscribe to a more minimalist style. I rarely buy new clothes. When I do, it’s a quality item, and I use the hell out of it.

Furniture: Another area where I’ve spent thousands. Brand new sets of night stands, coffee/end tables, kitchen tables, entertainment consoles, chairs, stools, and the list continues. These items can all be purchased for a fraction of the cost on craigslist, facebook, at yard sales or local auctions.

Recently, instead of paying $80-$100 for a fancy side table, we bought this vintage sewing table for $6 at an auction. I cut the legs so it’d be our desired height, and my wife painted it yellow ($4). I think I had it in my mind that I couldn’t use someone else’s stuff, but that’s completely ridiculous. I’m so glad I’ve realized it.

Buying an $800 Puppy

A smaller piece of guilt I have about our dog is that we bought her for $800. She’s a pure bread boxer, and she’s gorgeous. I just wish we had rescued instead. We got her shortly after we paid off all of our debt. We were spending a bit freely after having been “cooped up” for so long on our budget.

Much much bigger than that, is how much she costs us each year. Not just in food, medical, raw hides, bones, toys, but also the opportunity costs.

We can’t have a nice back yard. She is extremely mischievous, and she loves the smell of potting soil. So, she has dug up every single plant, bush or tree we’ve tried to grow. I did successfully build a raised bed, and we have a baby fig tree (fenced in) that she has been unsuccessful with infiltrating.

When we got the house, the back yard was basically dirt. I’d like to put grass back there and a sprinkler system, but honestly I’m afraid to invest the time and money for fear that she will cause damage to part of or the whole operation. So, sand lot it stays… although the centipede grass is creeping in from the edges of the yard so maybe in 7-8 years, we’ll have an established lawn.

Oh yea, she chews on brand new furniture, or scratches it up trying to get her ball out from under it. Another reason to buy furniture used and recondition it.

Going to Culinary School
From: Matt @ We’re All Poor Here

If you haven’t read Matt’s blog yet, check him out. I absolutely love his rawness and wit. He doesn’t mince words. Go check him out at

When asked to share any painful financial mistakes, Matt wrote:

Gosh. There are so many (mistakes). Culinary school is the biggest. The place I went to was $19,000 a year, just for tuition. I took loans out the wazoo to get the money to go. I graduated in 2007, and my first job was making $18,000 a year, working 6 days a week, 10-12 hours a day. I kept telling myself it would pay off in the long run. Five years later I finally made it to the position of executive sous chef.

I made $12 an hour.

Would I make more in NYC or Vegas? Sure. But the cost of living in those places is substantially higher, so it would end up being about the same.

I’ve literally been paying for this mistake since 2008. I’ll continue to pay for it for as long as it takes for these student loans to go away. Not a day passes without me thinking of what a huge fail this decision was.

I know one guy that I graduated with who’s still in food service. He’s bald. His body is jacked. He has an alcohol problem and does quite a few other recreational activities.

I don’t envy him at all. Seeing him in that situation hurts. I feel sorry for him and empathize with that situation. Because I was there. It took a long time but I finally got out of food service for good. And I haven’t regretted that decision for a second.

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Please go vote for my post in the Best of the Best

What About You?

Leave me a comment with one of your painful mistakes! Also, if you’d like your mistake to be featured on the site, I’ll write a Part 3 and include yours. Email me at

18 Replies to “Painful Financial Mistakes – Part 1”

  1. Another gotcha is this year’s model. A camera, car, or computer can all be tons cheaper if you get the remnants of the prior model year. Used running shoes aren’t a great idea, but last year’s model are FINE!

    And I couldn’t bear to take on the financial burden of a dog at all, much less paying $800 for the privilege. Wow!

    1. This is true! I bought last year models on my mattress, TV, and refrigerator. Great tip there! Yea, the dog has been a tough pill to swallow…

  2. Boxers for the win (except in the wallet). I’ve got a boxer too who also costs us a lot but I’d argue he makes up for it by being super adorable. I agree with the rescue dog statement though, and actually also have a rescue dog who has cost a lot both initially and ongoing. Being a mutt she’s just hardier than our boxer.
    I don’t have one big money mistake, instead, it would be a lot of small things. I used to be bad for buying too many new clothes and if I added up all those unnecessary purchases it would add up to a big mistake.

    1. Ah, they are super adorable, no doubt. Like you, I found it hard to come up with a huge mistake as well, but a few hours of brainstorming brought forth some goodies. I tend to be pretty optimistic so I let my failures go pretty quickly, and sometimes don’t remember them as such. Clothes are a big one!

  3. Similar to you, I signed up for 10 spin classes at a gym. I had never taken a spin class before, but I got a 50% off coupon from Groupon, so I thought I was way ahead of things. After I took the first class, I knew I had made a mistake. I took one more class but that was it. I should have just trialed for free one class to figure out that it wasn’t the best fit for me.

  4. I got stuck with a 3 year ADT contract because they sent a cute girl to my house. Then I had to fight with them because their sales pitch was misleading. They said my home owners insurance would go down so and so %, it didn’t. Two years later we finally parted ways.

    P.S. All you really need are the signs and stickers, share amongst yourself with friends and family. The stickers from my contract now appear on 3 different houses.

    1. Those sales people trained in high pressure sales tactics, and man it works. Good point on the stickers. I’d say a thief has no reason to go into an ADT house if there are 10 right next door with nothing posted.

  5. I have made several financial mistakes…the biggest investment mistake I made was to listen to advice of experts and purchase Fannie Mae stock before it tanked. I have blog posting on it, and there are even a few articles still online from that timeframe!

    Lesson learned the hard way! I listened to the advice of others and didn’t understand the investment. Now I invest in primarily index funds!

    1. PM, I do the same! Index funds are low-cost and capture the performance of an entire section (or even all) of the market. What’s not to like?

  6. I want a part 2 and I want to be in it . We didn’t buy our puppy but the rescue we got her charged $450 for adoption/vet fee/transport and we added another $500 for training. Dogs are mucho expensive.

  7. That Gym membership brings back memories lol. I did the same thing, except I think I paid maybe half of the price.

    Ive realized contracts usually aren’t my thing. From Gym memberships to cable TV, I try to avoid them.

    1. Yeah… I’ve literally never had another gym membership because of that. Scarred for life. My garage has slowly turned into a little gym in spite of Gold’s Gym.

      I cut cable for Netflix when it was mainly DVDs. I’m cool with subscriptions as long as I can cancel at will.

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