Financial Regrets, Do You Have Them?

by Katy on October 3, 2016 · 23 comments

This blog post first appeared over at

Unless you’re a fictional character, you’re likely to have a few financial regrets in your life. Hopefully they can be counted on a single hand, and if you’re lucky they’re long in your past. Either way, almost all of us have made cringe-worthy financial decisions, which can often follow us years or even decades into our adulthood.

When asked about their financial regrets, members of the popular Facebook group The Non-Consumer Advocate had these regrets to share:

Buying a house

Not surprisingly, people both shared that they regretted buying and not buying a house. While one woman reported her regret over “buying a money pit of a house,” other people regretted “buying too much house” or “buying a house before we were financially stable.” Specifically, people regretted “Paying PMI” (Private Mortgage Insurance) that comes with putting less than a 20% down payment onto a house.

On the other hand, holding off on buying a house can also lead to regret, as another person lamented that “I wish I’d bought a house before house prices became completely out of my reach.”

College and student loans

Although a college degree can lead to a meaningful and well paying career, one person regretted “getting a college degree that didn’t lead to a specific job/career. I chose based solely on interest and it’s pretty much worthless today.” Similarly, another person shared that “I regret going to college for a career where there is huge competition for few jobs and using a lot of student loans to do so.”

Of course, entire tomes could be written about student loan regrets, but one group member specifically regretted “taking so many student loans ‘for living expenses’ when I had a full scholarship! Now my husband is helping repay what I spent on dinners with my ex!” Another had the honest response that “by far my biggest regret is using student loans to buy clothes, a fancy keyboard, a car, etc.” Ouch!

But like house buying, the regrets swing to both sides as one woman looked back and shared the regret of “not getting a master’s degree when it was cheap.”

Considering that 40% of first time entering college students do not complete their bachelor’s degrees, it’s smart to think twice before choosing a major and taking out student loans.

General loans

Whether a borrower or a lender, there were ample regrets in this category as well. The practice of “co-signing a loan” was a common regret, specifically “both lending and borrowing from family.”


With the average wedding costing $32,641, it’s no wonder that couples regret the money spent on a single day. One former bride put it all on the line when she wrote that she regretted “a wedding that lived up to other people’s (who weren’t paying) expectations. Should have had my dang potluck and gone with a pretty sundress I could wear again.”

All the stuff

Throw a few things into your cart at Target and it adds up a bit, but multiply that action through the years, and it’s enough to create a bottomless pit of financial regret. People shared everything from “frittering away money on mindless purchases I didn’t need or even want very much instead of saving more.” to “my biggest financial regret would have to be buying so much needless stuff that I truly could have lived very nicely without over the years. Had I saved all of that money instead it would have been an excellent addition to my retirement nest egg.”

Parents are particularly susceptible to this regret as one mother shared that “much of the stuff I bought at Target when my kids were little – because that is just what people did . . . especially the plastic ‘crap’ that broke. Also, having too many things – to the extent that I did not know what I had.”

Of course, buying so much stuff inevitably leads to owning too much stuff which led to this person’s regret. “Buying. All. The. STUFF. And now wanting to get rid of it all.”

Not contributing to retirement/HSA

This one is a personal regret as I was in my job a full three years before anyone talked to me about the retirement plan and the employer match that I was qualified for. My heart drops into the depths of my stomach when I think of all the compound interest that I missed out on, especially since I’m now long vested in that same job.

I try not to feel too stupid, as this is a common financial regret as can be seen in this person’s similar story. “Not taking advantage of the employer 401k match at my first job out of college. I didn’t educate myself on what it was and didn’t put anything toward retirement. I kick myself when I think about how much I could have saved and how much it’ll cost me in the future for not starting earlier.”

At least I’ve kept my money squarely in my 403b unlike this woman who confessed to “emptying a $3000 retirement account in order to pay for preschool for my then 3 year old. (So stupid!!!)”

This person shared a HSA (Health Savings Account) regret related to her’s husband’s employer. “My husband was at his current job a year before we found out HSA was an option and his employer adds 1k to it every year.” Oops!

Credit cards

No piece about financial regrets could be complete without a focus on credit cards. Whether it’s the common story of “getting every single department store credit card out there and maxing them out and making only the minimum payments.” or “getting a credit card in college,” many people dig themselves into financial holes with credit card use. Others need to learn their lessons over and over again as evidenced by this woman who shared that she paid off, “my credit card when I got my portion of my father’s estate and charging it right back up. Dumbest move ever. I won’t let that happen again. My dad would have kicked my ass from the grave.”


Whether your financial regrets run from minimal to catastrophic, the important thing is to accept the past and do everything you can in the present to get back to financial wellbeing. Any maybe, just maybe you can learn from these people’s mistakes and avoid a regret to two.

Katy Wolk-Stanley

“Use it up, wear it out, make it do or do without.”

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{ 22 comments… read them below or add one }

Elizabeth October 3, 2016 at 2:22 pm

We made so many foolish mistakes when we were young. Buying a house before we were stable and mature enough, lost it. Had a small wedding, but still wish we’d simplified. Taking out loans our buying on credit unnecessary things that we thought we needed right after marrying. If only we could go back and do things over again. Thankfully we lived and learned. We were slow learners, but I’m glad we’re not where we used to be.


Krystal October 3, 2016 at 8:55 pm

I agree on the wedding! Even though we were out of debt and paid cash for our wedding, I would have just been as happy at the courthouse and putting that money toward retirement savings.


Elizabeth October 4, 2016 at 2:55 am

You and me both Krystal. Not to mention all the other wasted money over the years. Wishing we’d always been frugal and saved.


Beth October 4, 2016 at 6:03 am

I second the wedding thing. We didn’t spend a lot at all, but I wish I had done it much simpler (which would have made it even cheaper).


Elizabeth October 4, 2016 at 6:17 am

We spent very little on a small church wedding. Our biggest expense was the photography and flowers, thankfully didn’t need many flowers. I wore a borrowed dress, but like Krystal, I would have been just as happy with a court house our even small home wedding.

I wonder about people willing to spend thousands or even tens of thousands on a wedding these days. I just have to shake my head.

Gina October 3, 2016 at 2:45 pm

When cleaning out my mother’s basement after she passed away, I found a box of my financial documents from when I was a teenager, paystubs, cancelled checks, receipts and such. And a huge stack of paid receipts to BMG Music Club! Remember them?! They offered a large amount of free CDs (maybe 20) when you signed up, and you had to agree to buy so many more. Little did I realize they charged a fortune for those CDs you had to purchase, like three times more than at the store. Enough that the free CDs weren’t free anymore. I would like to have not wasted money on things like that, or credit card purchases for silly non-needed things, or cable TV for all of those years, or a landline way longer than I needed to, etc. All of those areas I try to be frugal in now.


Revanche @ A Gai Shan Life October 3, 2016 at 3:42 pm

Oh plenty, I was young and dumb once 🙂

I cosigned a car loan for my sibling which of course he stopped paying for within 2 years, I paid off well north of a hundred thousand dollars in debt for my family, I trusted family members with a significant sum of cash and naturally never saw that again. It’s almost a surprise that we made it through well enough to build up our savings and a strong financial foundation since.


BJS October 3, 2016 at 5:22 pm

I enjoyed this article, especially the quotes. My favorite was when the bride said, “should have had my dang potluck.” That made me laugh! When I was much younger I attended a wedding reception that was a potluck (the bride and groom were hosting the wedding themselves and neither of them had money, which they were quick to admit) and I remember it being a lot of fun!


Krystal October 3, 2016 at 8:53 pm

Great topic, Katy. I have a few regrets financially, for sure. I think I could have saved myself some pain if I would have learned about finances as a kid, but it wasn’t talked about unless it was a fight or a fleeting windfall in my home. We didn’t have much money growing up, yet my maternal grandparents were millionaires and very smart. I feel like through trial and error and a combining the “what to do” of my grandparents and the “what not to do” of my parents, I have made it to a fairly confident place. I still can’t believe I cashed out an IRA to take some post-grad classes, even though it wasn’t that much!


Lindsey October 3, 2016 at 8:55 pm

1. Buying a house and then deciding that I didn’t like it so sold it for a loss and moved into a new house. Did this THREE times! I figured out one day that these idiotic moves cost us $100,000.

2. Lending my brother and two friends money we never saw again…another $10,000 gone.

Luckily we wised up. Actually, I learned from my husband what idiotic things I was insisting we do and he learned to stop indulging me on big financial things. He nearly lost me once to an illness and I think it made him very soft hearted about me. He still is but thank God I grew up.

We recovered from my excesses early enough to be able to make up for them.


Amy K. October 4, 2016 at 3:15 am

I can identify with too many things on the list. Not sure whether I need to feel guilt afresh or feel better that I’m not the only person who has done these things?

I got in trouble with a credit card in college. Now I lecture my kids about it not being “free money”. I had student loans that, thankfully, between my parents, myself and my husband, we got paid off early in my marriage. But, after a promising start in marketing and graphics, I took a decade or so to raise two kids and here I am in my 40’s, unable to find a decent job. Wish I’d studied something different.

My husband and I paid for our wedding ourselves. From invites to honeymoon, it only cost us about $5,000. At the time, I thought a pretty wedding was important. Now I feel like even $5,000 to impress others is too much. My parents bought my gown and I regret that. It was beautiful, but it was $1,700! I wore it once! I can’t decide if I should keep it for my daughters or try and sell it.

We’re on our third home. I hate buying and selling homes, by the way. Expensive and stressful. We had to do it because of my husband moving jobs. I can’t decide if it was poor planning on our part, or just bad luck, or a combo? Twice it happened that a job we thought was permanent, fizzled out or led nowhere, or a department was axed and boom…he had to find something else. Our first home was brand new, so no real issues, but it sold at a loss. Our second home was a lot of house for the money (Ohio, rather cheap, we got excited) but turned out to be a money pit and barely held together. Had to spend so much money to fix it up, AND it sold at a loss. 🙁 Felt cheated on that one. That was four years ago and still recovering. We moved to South Florida, near Fort Lauderdale. I wanted a bungalow, three bedrooms and a pool in a nice neighborhood, with great schools. Some people would call this place tiny, and okay, it is, but it’s just enough space and easy to clean.

I am drowning in “stuff”. Why oh why did I need so many tchotchkes in my life? I honestly just want to live in a white box with a mattress and a lamp for the rest of my life. I want to sell everything.


Hobart Chic October 4, 2016 at 6:44 am

It sounds to me like you have done pretty well overall. I suggest reading Peter Walsh’s clutter busting books. I would sell your wedding dress as the chances that your daughters want to wear their mothers, by then dated, wedding dress on “their special day” is slim to non-existent. Let them ooh and aah over your photos instead and have their own dreams.


Amy K. October 4, 2016 at 8:40 am

Thanks for the advice. 🙂


Denise October 4, 2016 at 1:21 pm


I was really touched reading your post. It all sounds hard, but well done on finding a home that is “just right” – as that book, “Your Money or Your Life” says, it is all about your own version of “enough”.

I’d highly recommend Joshua Becker’s site,, as a good way of thinking through why and how to deal with all the stuff in your life that you don’t want or need, including time/scheduling issues around over-commitment.

Good luck.



Bee October 4, 2016 at 4:05 am

I have definitely made some financial mistakes — both big and small. Since hindsight is always 20/20, I have looked back long enough to try and learn from these mistakes. However, I try to concentrate on what I have accomplished, what I need to accomplish, and how I am going to get there. I cannot undo the past, but I can create my future.


janine October 4, 2016 at 5:24 am

We were both lucky and unlucky – I characterize it in that manner because many of our financial decisions were the result of luck rather than forethought.
Wedding – lucky – a fairly large affair – my parents paid for it, but also dictated how the whole affair would proceed. I was the daughter who advocated holding back a little! To be honest, my father was a businessman who felt obligated to host a “decent party” – and he loved to host parties.
Housing – Lucky again – we did buy a substantial house in a good neighborhood – definitely more than we could afford at the time. It has appreciated in value and has kept us for many years. We didn’t succumb to moving up during the g0-g0 days of easy credit and huge mortgages.
Credit Cards – unlucky – one year we suffered severe financial losses (self -employed) and husband took on credit card debt that took a while to pay back at very high interest rates.
Investments and Savings – neutral – we lived pay check to pay check for years without a thought that we could manage any savings. Eventually we took out IRA’s, invested in 403B’s and made a small profit on some vacation property we sold.
‘Target Syndrome ‘- guilty as charged. Too much un-needed stuff and indulgences such as eating out and new clothes for the kids.
I also took time out to raise a family – costly, but it makes for a smoother running household.


JD October 4, 2016 at 5:43 am

I have so many regrets, some of them being quite recent, even though I feel pretty savvy by now about being frugal. Sometimes it just takes an outsider or a new angle to realize I’ve been doing something so silly and wasteful all along, not even thinking.
Back in the day, my husband and I were both totally naïve about money. We both came from families which didn’t discuss money, invest, or save much. I blew a small private student loan (on a purebred dog!), he took a loan out against his 401K for a tractor, ouch, and then his company changed hands and all loan paybacks were cancelled, so we lost that amount in his 401K plus had to count it as income and pay a penalty on it, double ouch. We bought far too many things on “time.” We didn’t move to get better jobs when maybe we should have, so we were stuck in low paying jobs and living paycheck to paycheck for far too long. We bought a mobile home, which is a real money pit and worthless when you try to sell it without the land. So many bad decisions! Slowly we have recovered, but we’ll never have as much in retirement as we could have had if we’d been smarter. Still, we have a real, if small, house that is paid for, a 401K and Roth IRA with some money in them, both kids graduated from college with no student debt, and we have enough to pay our bills and still save a little. I have regrets, but I have successes, too.


Mrs. Picky Pincher October 4, 2016 at 5:50 am

I do think I have a few financial regrets.

I absolutely don’t regret owning a home. It’s been a dream for Mr. Picky Pincher and I ever since we got married, and I’m so happy it’s finally become a reality. 🙂 In our area, houses are cheaper than rent, and it also means we can do urban homesteading to save money on food costs.

I do regret my student loans, though. I chose a marketable major, but I went to a private college, which means my student loans were pretty pricey. I would go to college if I could do it all over again, but I would have gone to community college first and then transferred to a public university for my degree.

We were fortunate enough to pay for our wedding and honeymoon in cash, but it was still a lot of money!! If we had just gone with a simple courtroom ceremony, we could have saved that money and bought a house much sooner.


Beth October 4, 2016 at 6:10 am

1. I regret spending so much money on a degree that I’m not even using.
2. I regret our entire first year of marriage, as far as our finances go. We paid $1000/month to live in an apartment in a nice part of town, ate out at sit-down restaurants every weekend (I wish I was kidding), and had all of the latest stuff. When hubby was laid off, we had a very rude awakening. At least now we know better, and we have learned to be able to live off of only one income.
3. I regret buying so much stuff. Even though the majority of my shopping is at the Goodwill Outlet, I still sometimes come home with things that I don’t need.

I don’t focus on the regrets though. I try to learn from them and keep moving forward. Thanks, Katy (and her readers) for providing a good source of motivation!


Vickie October 4, 2016 at 6:59 am

Oh yes, plenty of regrets – the two worst 1) student loans and 2) credit cards. I finally figured out I’m an impulse/emotional spender. I stay out of the stores now, but I wasted a lot of money over my lifetime. I’m trying to mend my ways now, but paying dearly for past mistakes.


chris October 4, 2016 at 8:27 am

There are many expensive things (having three kids is one! ) in our past that we don’t regret…but ever having credit cards was dumb. And buying a house at 23 without an emergency fund…so dumb. It is all paid off now, including the house, so we are able to go into our forties making better decisions. That, at least, feels good.


Penny October 4, 2016 at 9:33 am

I have made so many financial mistakes in my life that, if I kicked myself for each and every one, I wouldn’t be able to sit down for years to come.
The one thing I don’t regret at all though, is buying a house. I was (for once) reasonable and bought something within my means. With the interest rates being so low at the moment I can double my mortgage payments every month and I should be mortgage-free much sooner than expected. Even if I wanted to rent a single room, there is no way I could afford it for the same money.


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