let's see:

Not participating in ROTH IRA
Not contributing the max to 401K
Taking money out of 401K

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.

which public school did your children attend? the PS seems important.

Anonymous wrote:Stop investing in the market after the 2008 crash.

Ugh. Same. We were never in heavily, but pulled everything out just before the crash. Felt lucky. Finally got back in just before the correction in 2018. Ugh. But thankfully we stayed in, though with very conservative allocations. We are doing better now, and gaining traction. But man, it is hard to take how much we missed out on.

Woulda, coulda, shoulda.

I’ve managed our money pretty well over the years, but everyone makes mistakes. Looking back, my biggest mistake was my ill timed purchase of a vacation rental home in the Outer Banks. I bought it right before the market crash of 2008 and its value dropped by nearly 50% almost overnight. I sold it close to 10 years after I bought it at a huge loss. Fortunately, because it was a rental property I could deduct the loss from my taxes so that cushioned the blow by close to half, but I still lost a couple hundred thousand dollars.

Stop investing in the market after the 2008 crash.

Anonymous wrote:

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.

I did the same thing. Well, similar. I ignored a scholarship from Notre Dame and went to a school that was ranked lower because I wanted to move to that city. It all worked out, I loved my law school years, but it wasn't the best financial decision to just ignore the full scholarship offer.

This is insane. I could see turning down Notre Dame for a higher ranked law school, but to go to a lower ranked school and pay more just because it’s in the city you want to practice in makes zero sense. The Notre Dame degree travel well.

Anonymous wrote:Not buying more aapl.
Not buying bitcoin when it first came out and I had been to a few seminars.

Oh I bought a bunch of Apple about 15 years ago and when it didn’t perform quickly I sold it all! Dum da dum dum

First mistake and lesson was - getting into a 7K credit card debt in 7 months, 30 yrs ago, when we were new immigrants with nothing and an HHI of 30K. Of course, to compound the problem, we neither had a budget, nor we tracked our money. Also we were paying a quite high interest rate (8%). We had no credit history and no one was giving us a cheaper rate because of our work visa status.

I paid it in 2 years after going into extremely frugal money management while still outwardly maintaining a white collar lifestyle.

Not buying more aapl.
Not buying bitcoin when it first came out and I had been to a few seminars.

Investing in a friend’s family’s start up instead of the stock market. We were so stupid, it seemed like a sure thing, all our friends were dying to put money in, convinced they would sell the company in a year and we would get our money back ten fold. A decade later and we never got a cent back and never will. We’d have been better off hiding the money under a mattress.

Similar to a PP's. Not paying attention to investing.

Conservative allocations in 401Ks. Had no debt other than mortgage, paid off credit cards every month, didn't spend more than we made, so felt really good. Only to realize later that we should have been doing a much better job of making money work for us.

And like the PP, we are all over it now, but it can get to me re: all the years we wasted.

Almost 20 years ago, we had an opportunity to buy “friends and family” stock at pre-IPO price, about $15 per share. We passed. I can’t even bring myself to name the company.

Not starting investing in 30's.
Not buying real estate in 90's.
Taking a break from career.

Nothing big, but buying three properties. Had we just kept renting and invested all the extra money it took to buy them, we would have couple of million dollars right now.
None were under water when we sold them. None had anything really wrong with them and weren't money pits. One even had renter for over decade. None were our dream home or even fit out family.
I bought the homes for living at some point in life. Had I known anything about stock market, I would have gone with the market. Sold all three in last fours years and I'm soon catching up to a million in the market. The other million will have to wait.

Anonymous wrote:

Anonymous wrote:Mine is the opposite, but I regret not spending a bit MORE on my house. I was cheap and didnt want to add on a garage... I regret that so much!

This. We heavily consider moving to a nicer home in 2018-2020 and wish we had just done it. Now we are staying put.

Same. Bought below our budget in 2019 to get to know the area.

Wish we would have been more aggressive. Upside is we are doing very well financially due to our low mortgage, but never imagined us living in this house long term.