What were your biggest financial mistakes?

[Anonymous]

This thread is making me glad I got AAPL. Thought about buying it for two years, then finally did in 2015. Felt like it was "too late," but still holding onto it.

As for regrets, we are still renting in our 40s. I wished we pushed harder to buy a place a few years back when rates were lower and prices weren't sky high. Feels incredibly out of reach to buy anywhere these days.

[Anonymous]

Anonymous wrote:This thread is making me glad I got AAPL. Thought about buying it for two years, then finally did in 2015. Felt like it was "too late," but still holding onto it.

As for regrets, we are still renting in our 40s. I wished we pushed harder to buy a place a few years back when rates were lower and prices weren't sky high. Feels incredibly out of reach to buy anywhere these days.

Oh hey. Us too! Have AAPL, but don’t own.

[Anonymous]

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.

[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.

This is horrifying. I hope it’s a troll, it’s that bad.

PP, if you’re not a troll—I am so sorry. This board is a terrible place for financial advice except in very limited circumstances. You have to know what they are to know when it is OK to consider ideas floated here, and that requires basic finance education most people don’t get.

[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.

It's a viable method, but needless to say, you invested in the wrong stock. I wouldn't have felt comfortable buying anything else than the market index when using leverage.

[Anonymous]

Worrying about capital gains tax rates when owning a stock I very well knew was speculative.

Back in the dotcom boom I bought a stock for $5/share in March 1999 and it was trading at $500/share in March 2020. I knew it was kind of crap but thought...if I just wait 2 more weeks I get the LT cap gains rate.

Well, if you recall, Nasdaq started crashing early March 2000. I did end up selling the stock at $150/share, so no crying for me. If the stock had simply gone from $5 to $150, I would have been happy as a clam. However, knowing it was at $500 was painful.

The company ended up dropping down to like $0.25/share, though did end up surviving.

[Anonymous]

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.

[Anonymous]

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!

[Anonymous]

Anonymous wrote:In 2000 I sold $5k in the Vanguard Index 500 and split it between Janus Enterprise and Janus Global Life Sciences. Floundered for a decade and then I bailed. Should have left it in the index.

Dad/financial advisor: “If that’s the most expensive mistake you make, count yourself lucky.”

Remember those days---watched it go up and was impressed, waited too long to get out as well.

[Anonymous]

Anonymous wrote:Going to law school at the best one that accepted me T-15, instead of taking a near total tuition free ride at a respectable T-25 school.

YEP! ugh.

[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.