What is the biggest money mistake you've made?

**disneysteve** · 12-15-2025, 05:36 AM

First thing that came to mind was buying whole life insurance.

We lucked out on that one, though. There was a class action lawsuit against the insurers for misrepresenting whole life as a good investment and they lost the case. We got back everything we had paid in. The sad thing is that insurance companies never stopped doing it. They still promote whole life as an investment vehicle which it is not.

**ua_guy** · 12-15-2025, 06:32 AM

Cars are my weak spot. I don't make "stupid" decisions there, but I allocate and have more resources tied up in vehicle ownership than most. It's a hobby, and, I have way too much vehicle and too many vehicles for my actual needs. But I do that with my other metrics tracking the way I need them to be. If my primary goals needed attention or weren't making the needed progress, the cars and that hobby would disappear.

**james.hendrickson** · 12-15-2025, 07:12 AM

So for me it was: divorce.

My ex wife and I had like 4 or 5 properties in Washington DC, and like an idiot I lost all of them in the divorce. Its taken years to recover from that loss.

**kork13** · 12-16-2025, 12:13 AM

I spent too much money on my first car in college -- bought it new, and borrowed $12k at an absurd interest rate (>10%?) ... In spite of my father trying to convince me otherwise.

I've made a few poor investment choices, each of which have cost me a few thousand dollars.

Those are the mistakes that stick out the most. There certainly have been other times that I could have been more efficient or financially smarter (probably some of the houses we've bought/sold/rented over time) ... But I wouldn't call any of those things a mistake.

**srblanco7** · 12-16-2025, 01:37 AM

My first two cars post-college were brand new and financed. Now, when we can afford to buy new, my irrational hatred of car payments and/or spending too much on vehicles means we only purchase 2-3 year old new to us vehicles.

Tried market timing ahead of the dot-com market bubble. As I recollect, didn't get it right on either end - exit timing nor re-entry timing.

Thankfully, got a few things right along the way as well.

**LivingAlmostLarge** · 12-18-2025, 10:08 PM

timeshare. Need I say more?

**PatientSaver** · 12-19-2025, 06:47 AM

I would have to say going to law school, finishing 1 year and then dropping out becus I wasn't "sure" I liked it. I should have either never have gone at all, or stuck it out and improved my earning ability.I think I also picked the wrong school although the setting in Boston was lovely. I wish I'd had a mentor who could have shown me the many different jobs you could get as a JD and not have to step inside a court room.

**Fishindude77** · 12-19-2025, 07:26 AM

Most of the classics:
Leased automobiles
Borrowed for automobiles
Bought boats & campers
Whole life disguised as a good investment tool
Ran up credit cards and didn't pay in full

Thankfully, all that stuff is in the rear view mirror.

**ua_guy** · 12-19-2025, 07:37 AM

Mistakes are easy to make, but about the things we didn't do that ended up costing a mint?

Deciding we wouldn't be dragged around the country for work, and being far away from family has cost us dearly. But we love where we live, family is everything, and we're doing well enough. We'd likely be several million ahead at this point if we had followed every "next" job opportunity that presented itself along the way.

**LivingAlmostLarge** · 12-19-2025, 12:00 PM

selling company stock to properly diversify shouldnt have would be millions richer. like at least $5m.quitting work and taking a year sabbatical that was lost income of a lot.both investment and draining our savings. but that is not a money mistake. we had reasons for both that were legitmate and smart.

Timeshare? well there is no justification except being young and dumb

**srblanco7** · 12-20-2025, 03:58 PM

Originally posted by Fishindude77 View Post

Most of the classics:
Leased automobiles
Borrowed for automobiles
Bought boats & campers
Whole life disguised as a good investment tool
Ran up credit cards and didn't pay in full

Thankfully, all that stuff is in the rear view mirror.

Nice greatest hits list. If you added a bit of market timing, you’d pretty much have it covered!

**Like2Plan** · 01-15-2026, 06:26 AM

Long story warning! I'm not sure this is my biggest mistake, but it is one I'm still dealing with now.....

Starting in the 1980's I purchased DRIP stocks. Since I wanted to be diversified, I purchased a lot of different companies mostly resulting in a few shares of this, a few shares of that. Sometime around the 2008 downturn I sold almost everything and purchased an index fund in a brokerage account which simplified my life quite a bit. The almost part is what I'm dealing with now.

One of the companies was Dominion Resources (D). When we first signed up for this stock the company itself was running the direct stock purchase. They had a real sweet deal where you would pay in a set amount each month and at the end of the year they would pay interest on the money and then the savings plus interest was used to purchase stock at the average price. We did that for a couple of years and then on just reinvested the dividends. Anyway, when I was simplifying things I transferred almost all the shares to a brokerage account. I left 1.3 shares behind so in case it didn't work out with the brokerage I could easily transfer everything back. I can't say the brokerage has been 100% satisfactory, but it has been a PITA to track the earnings on the 1.3 SH (they don't send 1099's on under $10.00 of earnings so one has to remember to put that on the taxes every year).
Meanwhile, Dominion Resources must have thought it was a PITA to manage the direct purchase plan because they transferred the management over to Broadridge and more recently Computershare. (BTW, Computershare has a horrible user interface and relatively high fees: $25.00 to make a trade plus a couple of cents per share.) Anyway, we sold the 1.3 shares! One more year of tracking (the sale will go on 2026 taxes.)

Now, I just have 2 more vestiges of my DRIP folly days which are a little more difficult to unwind. They involve Disney (DIS) stock certificates. My first stock purchase was DIS. I received a stock certificate from Disney. I liked the art work on it and I thought I might frame it some day. Meanwhile, Disney stopped issuing stock certificates. Disney also switched their direct stock purchase plan over to Broadridge and then Computershare. I don't want to surrender my stock certificate (which I believe I would have to do in order to transfer). All the rest of the shares that were held in book format were transferred to my brokerage account. I would like to simplify things (everything kept at the brokerage), but since I still like the artwork on the stock certificate I think I am stuck.

The other one involves my son. When he was a kid--we made DRIP investments for him, too. When it was time to transfer everything over to him--I advised him to sell everything and put the proceeds in an index fund. If he still wanted to own a particular stock he could buy it back. (One major reason for this was pre-2012 one had to track the basis for stocks and so keeping them would make his future taxes more complicated ) He also had 1 share of Disney in certificate form. When he found out that he couldn't get another certificate he didn't want me to transfer ownership over to him.... So, I think I am really stuck on this one.

**disneysteve** · 01-15-2026, 02:58 PM

L2P you could go on eBay and buy a Disney stock certificate for display and then cash in the ones you own.

**Like2Plan** · 01-15-2026, 03:26 PM

Originally posted by disneysteve View Post

L2P you could go on eBay and buy a Disney stock certificate for display and then cash in the ones you own.

I did buy a specimen share from scripophily (I guess it is a proof?) with that idea in mind, but it didn't have the same impact. Are the ones on eBay real stock certificates? I might eventually let my certificate go, but I don't think DS ever will.

What is the biggest money mistake you've made?