While it is common to make mistakes and learn from them, some mistakes leave a lasting impression. A user asked the forum, “What is your most expensive mistake?”. Let’s look at the top responses from the forum.


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“I moved in with the wrong people and lost 95% of my possessions. It’s a long story, but basically, they changed the locks while I was at work, and I couldn’t get to anything that proved I lived there, and then they moved everything in a day with a moving service.

I can’t even track them down because they were using false names and were apparently subletting instead of owning, and they used false names when they rented the property. It was the most messed I’ve ever been in my life.”


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“Student loans, failed my first semester of college because I didn’t ask for help, lost all my scholarships that paid 90% of my cost of attendance, wasted tens of thousands of dollars in student loans that semester and the next semester.

I had to pay extra fees for required remediation courses that had to be taken on top of (not instead of) my retakes that next semester that I had to take even more loans out for to make up for the lost scholarships.”


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“Marrying my wife.

She’s like a tropical storm – came wild and wet, and when she left, she took the house and the car.

I wish that was a joke, but it wasn’t.”


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“In 2009 (or so, can’t remember the date, but sometime between 2008 and 2011), my buddy got really into Bitcoin. It was back when bitcoin cost like $5 per coin.

I didn’t understand it, I still don’t really understand it. But back then, I had no desire to learn about this thing that seemed like a fad/scam.

He did, however, convince me to invest, if only to shut him up.

So I threw $50 his way and told him to get me 9-10, and he set me up with the bitcoins and put them on a USB for me. Which, again, is another thing I didn’t really understand or care about.

So I tossed that USB in a box and didn’t care about it.

When I later moved, I was packing things and came across the USB I had labeled with something stupid. I still didn’t care about Bitcoin and offered it to the guys I was living with.

I remember one of them saying, “Dude, are you sure Bitcoin is at 10.”

I truly didn’t care enough to learn about Bitcoin, or even what to do with the USB to get the bitcoins off of it (or whatever you do with it) to bother figuring out how to recoup my $50, so I shrugged, tossed it at him, and moved out.

Queue the years that followed when I learned that my apathy and laziness had me give away what could have been today, something like $ 350,000 CAD, or closer to $850,000 at its peak.

So, yeah. My biggest financial mistake was giving away that $50. Could have really used that $50 over the years.”


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“Not getting a handle on my mental health when I was younger.”


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“Selling my condo eight years ago to move in with my now ex gf.”


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“I took a leave of absence from massage therapy school. They said if you DONT call within three months to say you’re not coming back, you have to pay full tuition (10k, and this was 2010). Well, guess who didn’t call within three months?

The reason I even took the leave of absence was because I had attempted suicide. So I just wasn’t in the right headspace. Anyway, I finally got it all paid back a few years ago, but with no massage license to show for it.”


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“Not taking better care of my teeth and drinking too much soda. They are in decent shape now, but I’ve had to spend thousands getting them there.”


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“I’m in Finance. I bought 100 shares of a little company because it was annoyed that Blockbuster charged me $88 in late fees. With this, I could watch them whenever I wanted for a flat fee each month, and as a bonus, they actually mailed the DVDs to you in the mail, you didn’t have to drive to town and go inside and rent them. I thought it was a cool idea.

We didn’t really have much money back then, so when we budgeted poorly I sold them for a $2000 profit. I was kinda happy about too, lol. Damn, Netflix. I sure could use that $700,000 I missed out on.”


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“Chasing girls and relationships in my teens, twenties, and early thirties out of immature neediness. Burned a lot of bridges and hurt a lot of people. That and just being brutally immature, to begin with.”


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“Easy. I worked at Citibank. When the collapse happened. The stock dropped to $1.00.I joked that a few years ago, I earned one share, which was worth $52.00 at the time, and I let it ride as if it was just a dinner.

Someone on my team and I were talking and he said would you use your 401 to buy stock? I said I wasn’t sure. I said I don’t think it’ll collapse. I had $35K in my 401k. You could move it instantly. I chose to sit pat.

He used his to buy stock at $1.00. I left Citi weeks later. A few months after that, it was back to $50.00. I was a fool. It tears me apart to know that my cowardice cost me an early retirement.”


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“Doing an art theory degree because it was prestigious – now I am still paying it off 20 years later, never having worked a second in a gallery or art dealership. Only $15,000 to go.”


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“Opening a business that went broke in 6 months left me 120K in debt.”


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“Going off the deep end and spending my divorce money from selling my house on cocaine, hookers and gambling.”


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“Wasting money on a huge wedding where barely anyone remembers anything. Should have saved it for a house.”


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“I bought a house in Colorado(I am European) because I thought I was moving in with someone I loved immensely.

Not only did I not move in with said person, but even after four months of trying to get him to, he never showed up.

So now I have a fully furnished and stocked home in a state I visit at will and when my daily life back here in Europe allows.”


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“I bought a florist shop. Two years later, we had a recession, and I lost it and all the money that went into it. Flowers are a luxury item, and people don’t buy flowers in recessions.”


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“Buying a used Land Rover. Nothing but major issues and thousands spent on repairs.”


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“$2000 for a certificate that’s only good at the place I work at, and I can no longer get the job that requires it.”


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“Buying a Mac for programming and then discovering that it’s very limited, especially if you wish to have a program that works under Windows and other platforms or processors.”

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This article was originally published on Mrs. Daaku Studio.

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