What were your biggest financial mistakes?

[Anonymous]

1) sticking with a stock that shot up in value right after its IPO. We rode it all the way down to zero.

2) not knowing that RMDs for inherited IRAs are a thing or that you pay 50% excise taxes when you don’t take them.

3) leaving $100k in a checking account for many years.

4) not realizing that tuition tax breaks were income capped.

5) not realizing that you get basically zero deduction for medical expenses.

[Anonymous]

Anonymous wrote:1) sticking with a stock that shot up in value right after its IPO. We rode it all the way down to zero.

2) not knowing that RMDs for inherited IRAs are a thing or that you pay 50% excise taxes when you don’t take them.

3) leaving $100k in a checking account for many years.

4) not realizing that tuition tax breaks were income capped.

5) not realizing that you get basically zero deduction for medical expenses.

Wow…..this is both a humblebrag or just a brag and an admission of cluelessness.

[Anonymous]

Anonymous wrote:Not moving Mom out of State of Maryland. Considered moving Mom to Florida but Covid hit and she was getting good care in Maryland (late stage alzheimers.)

State of Florida estate taxes----"0$."
State of Maryland estate taxes----will be in the millions

Mom is getting good care so there is that and her quality of care would not be as good in Florida.

My FIL moved his late stage Alzheimer's mom from NJ to DE for this reason. Felt very cold at the time but honestly she was too far gone to know or care where she was and it allowed her to pass on millions more dollars than she would have if he hadn't bit the bullet.

[Anonymous]

Anonymous wrote:I'll start:

1. When we bought our house two years ago, the interest rates just began to increase. So our mortgage rate is 5.5%. We could have bought it down to 4.5% if we had paid an additional $60k for a couple of points, and over the course of the loan that would have saved us $600k (we have a crazy high mortgage loan). But we thought that we could soon refinance into a 3.5% interest rate, so did not take that deal...

Now our plan is to pay off the mortgage aggressively, even though we would invest in the stock market if we had a lower interest rate.

2. We should have moved to our current area way sooner; then we could have bought a house way sooner and cheaper.

Same. If we had started looking two years ago we would have been able too stay in our neighborhood, but when we bought last year, we were priced out by several hundred thousand dollars

[Anonymous]

Anonymous wrote:I’ve said it here before and I’ll tell the story again, in case it helps some young person make a better choice.

When I got my first professional job right out of college they offered a good retirement 401k match if I filled out the form and brought it to HR. I never did that. So for the first several years of my professional working life, when my expenses were rent in an apartment with many roommates, lots of beer and bar money, and travel to bachelorette parties, I saved zero for retirement.

I eventually got an MBA and started saving 5 years later than I could of, never taking advantage of years of matching funds at a time in my life I wouldn’t have missed them and they had the longest to compound.

I refuse to do the math on how much I missed out, but I think it’s at least a year or two of retiring earlier.

COULD HAVE.

[Anonymous]

Anonymous wrote:

Anonymous wrote:Sending my kids to private school for 6th-9th grades. Biggest waste of money (almost $350K+). Last 3 years in public HS and both went to T-20 colleges and are now doing great in their careers.

+1

Same mistake. Public high school has been better both academically and financially since we pulled from private middle school.

+1

[Anonymous]

Same as some of the other posters. Too conservative when I bought the house and now can't afford to move up despite the equity gains. On the other hand, I do have a 2.75 and incredibly affordable mortgage and still in a nice area. But I still occasionally think only if I'd been willing to spend 15% more as the agent was saying I could do, I'd be in the house and location that would make me happy for life.

Other regret is leaving too much cash in a checkings account for years and letting inflation eat it away. Have moved most of that money out into various funds and money market account and only keep 5k in checkings.

[Anonymous]

Anonymous wrote:Taking out a $300K second mortgage in December 2020 and then using all of it to buy PYPL stock. We bought 1200 shares at $250 per share and now have only 500 shares remaining worth a measly $30K. We ended up selling 700 shares throughout 2022-2023 at a huge loss just to make our payments on the second mortgage.

We have 27 years of $1300 payments remaining and maybe 2 years of runway in remaining stock until we’re insolvent.

I never would have done this before, but so many people on DCUM were going on and on about refinancing at historically low rates and using the leverage to invest.

Yes, but why Paypal? Any other one would have been better.

[Anonymous]

Anonymous wrote:Posted before, still applicable, sold asset, dh talked me into putting bulk of it into bitcoin mining. 500k. Mining fees are 6k a month that we’ve been paying with remaining assets money. Crypto winter anyone?!?!?! Now it’s having a rally, hope it holds!

Bitcoin has cycles. It holds and then it comes down. Then up again and then down.

[Anonymous]

Anonymous wrote:Taking out a $300K second mortgage in December 2020 and then using all of it to buy PYPL stock. We bought 1200 shares at $250 per share and now have only 500 shares remaining worth a measly $30K. We ended up selling 700 shares throughout 2022-2023 at a huge loss just to make our payments on the second mortgage.

We have 27 years of $1300 payments remaining and maybe 2 years of runway in remaining stock until we’re insolvent.

I never would have done this before, but so many people on DCUM were going on and on about refinancing at historically low rates and using the leverage to invest.

Yikes.

If only you put that in Bitcoin instead.

[Anonymous]

Anonymous wrote:

Anonymous wrote:Taking out a $300K second mortgage in December 2020 and then using all of it to buy PYPL stock. We bought 1200 shares at $250 per share and now have only 500 shares remaining worth a measly $30K. We ended up selling 700 shares throughout 2022-2023 at a huge loss just to make our payments on the second mortgage.

We have 27 years of $1300 payments remaining and maybe 2 years of runway in remaining stock until we’re insolvent.

I never would have done this before, but so many people on DCUM were going on and on about refinancing at historically low rates and using the leverage to invest.

Yes, but why Paypal? Any other one would have been better.

PayPal was the very definition of a stock market bubble. I suppose when it was skyrocketing during early COVID it seemed like the entire world was transitioning to online transactions and investing here was a no-brainer. But then it crashed just as fast. It is hard to see a bubble when you’re looking through it from the inside.

[Anonymous]

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:Taking out a $300K second mortgage in December 2020 and then using all of it to buy PYPL stock. We bought 1200 shares at $250 per share and now have only 500 shares remaining worth a measly $30K. We ended up selling 700 shares throughout 2022-2023 at a huge loss just to make our payments on the second mortgage.

We have 27 years of $1300 payments remaining and maybe 2 years of runway in remaining stock until we’re insolvent.

I never would have done this before, but so many people on DCUM were going on and on about refinancing at historically low rates and using the leverage to invest.

Yes, but why Paypal? Any other one would have been better.

PayPal was the very definition of a stock market bubble. I suppose when it was skyrocketing during early COVID it seemed like the entire world was transitioning to online transactions and investing here was a no-brainer. But then it crashed just as fast. It is hard to see a bubble when you’re looking through it from the inside.

Yes, but $300k into one stock? I bought Tesla as it was going up like a rocket. Don't listen to DCUM, but Bitcoin is on its cycle, right? Let's hypothetically say you are buying half a Bitcoin now (don't) with the $30k and see where it goes from now to August/ September 2025.

[Anonymous]

Anonymous wrote:

Anonymous wrote:1) sticking with a stock that shot up in value right after its IPO. We rode it all the way down to zero.

2) not knowing that RMDs for inherited IRAs are a thing or that you pay 50% excise taxes when you don’t take them.

3) leaving $100k in a checking account for many years.

4) not realizing that tuition tax breaks were income capped.

5) not realizing that you get basically zero deduction for medical expenses.

Wow…..this is both a humblebrag or just a brag and an admission of cluelessness.

What part of this list of financial irresponsibility and cluelessness seemed in any way like bragging?

[Anonymous]

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:Taking out a $300K second mortgage in December 2020 and then using all of it to buy PYPL stock. We bought 1200 shares at $250 per share and now have only 500 shares remaining worth a measly $30K. We ended up selling 700 shares throughout 2022-2023 at a huge loss just to make our payments on the second mortgage.

We have 27 years of $1300 payments remaining and maybe 2 years of runway in remaining stock until we’re insolvent.

I never would have done this before, but so many people on DCUM were going on and on about refinancing at historically low rates and using the leverage to invest.

Yes, but why Paypal? Any other one would have been better.

PayPal was the very definition of a stock market bubble. I suppose when it was skyrocketing during early COVID it seemed like the entire world was transitioning to online transactions and investing here was a no-brainer. But then it crashed just as fast. It is hard to see a bubble when you’re looking through it from the inside.

Yes, but $300k into one stock? I bought Tesla as it was going up like a rocket. Don't listen to DCUM, but Bitcoin is on its cycle, right? Let's hypothetically say you are buying half a Bitcoin now (don't) with the $30k and see where it goes from now to August/ September 2025.

I would’ve bought Bitcoin 6 months to a year ago. I wouldn’t buy Bitcoin now.

[Anonymous]

Anonymous wrote:1) sticking with a stock that shot up in value right after its IPO. We rode it all the way down to zero.

2) not knowing that RMDs for inherited IRAs are a thing or that you pay 50% excise taxes when you don’t take them.

3) leaving $100k in a checking account for many years.

4) not realizing that tuition tax breaks were income capped.

5) not realizing that you get basically zero deduction for medical expenses.

Be thankful that you don't. Our medical expenses are incredibly high and the deduction is basically $0.20 on the $1.00. I'd rather not have enough to deduct.