Mostly I’ve been very lucky with finances, but the one thing I regret is not putting more straight into college savings when my kids were born. We didn’t have a lot but did have about $10k that I earmarked for college but didn’t invest it.

Buying this money pit of a house.

Leasing a car for X months, on the idea that I was "saving" a certain amount due to a rebate. I ended up spending a ridiculous amount per month in the lease, and spent three very long, very frustrating weeks trying to pay off the lease with a loan. The lease financing company was a nightmare to deal with but even worse was the dealership from which I leased/bougth the car. Slime bags. Leasing a car is stupid.

Didn’t start to save for retirement until I was in my late 30s. I didn’t have particularly good job before then and my spouse was still in grad school so it’s not like we could’ve saved a lot, but anything would’ve helped.

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.

I bought an expensive piece of art while manic. Saw the work of the artist hanging in a window at a gallery and wandered in off the street and bought the damn thing. It cost so much I ended up unable to make my credit card payments and my very sweet boyfriend (now my DH) took pity on me and just paid it off. I absolutely hate the darn thing now and let's just say it didn't appreciate, lol. I've looked into selling it and couldn't; it's worth nothing. Ugh.

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.

Anonymous wrote:1. Signing up for credit cards in college when they came to campus and set up a "free tshirt with application" booth. Evil geniuses!
2. Getting a timeshare. We used it twice in 8 years, could never figure out how to rent it to cover the costs, and spent 4.5 of those years trying to sell it, which we eventually did for $1.

Time shares in any form are a scam.

So many.

Picking a career that is not lucrative. I love what I do, but it doesn't pay the bills.

Not saving for retirement enough.

Doing an expensive grad degree when I could have gotten tuition reimbursement if I had switched employers and done the degree part time.

Not putting our bonuses and wedding money towards a down payment and have no real estate to speak of and don't know if I can ever afford it now.

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. Signing up for credit cards in college when they came to campus and set up a "free tshirt with application" booth. Evil geniuses!
2. Getting a timeshare. We used it twice in 8 years, could never figure out how to rent it to cover the costs, and spent 4.5 of those years trying to sell it, which we eventually did for $1.

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’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.

I didn't invest in my company's 401k when I first graduated from college because I didn't know retirement savings were important then. Where I grew up everyone lives off social security.

I also blew a ton of stupid money on restaurants and taxis when I got my first good paying job.

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.